cas 2849-81-2, N-TERT-BUTYL-P-TOLUENESULFONAMIDE

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A novel synthesis of 3-aminoazetidines by ring transformation of 2-(bromomethyl)aziridines
A one-step approach to the biologically interesting 3-aminoazetidines is described. The reaction concerns a ring transformation of 1-arylsulfonyl-2-(halomethyl)aziridines with aliphatic amines under various reaction conditions. (C) 2000 Elsevier Science Ltd.
Karikomi, Michinori,De Kimpe, Norbert
p. 10295 - 10298
(2000)
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Access to 1-Phospha-2-azanorbornenes by Phospha-aza-Diels–Alder Reactions
The unprecedented phospha-aza-Diels–Alder reaction between an activated electron-poor imine and 2H-phospholes yields 1-phospha-2-azanorbornenes in a highly chemoselective and moderately diastereoselective reaction. The intermediate 2H-phospholes, which ac
Wonneberger, Peter,K?nig, Nils,Kraft, Fabian B.,Sárosi, Menyhárt B.,Hey-Hawkins, Evamarie
p. 3208 - 3211
(2019)
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Development of an Imine Chaperone for Selective C-H Functionalization of Alcohols via Radical Relay
The design of a radical relay chaperone to promote selective C-H functionalizations is described. A saccharin-based imine was found to be uniquely suited to effect C-H amination of alcohols via an in situ generated hemiaminal. This radical chaperone facilitates the mild generation of an N-centered radical while also directing its regioselective H atom transfer (HAT) to the β carbon of an alcohol. Upon β C-H halogenation, aminocyclization, and reductive cleavage, an NH2 is formally added vicinal to an alcohol. The development, synthetic utility, and chemo-, regio-, and stereoselectivity of this imine chaperone-mediated C-H amination is presented herein.
Nakafuku, Kohki M.,Twumasi, Raymond K.,Vanitcha, Avassaya,Wappes, Ethan A.,Namitharan, Kayambu,Bekkaye, Mathieu,Nagib, David A.
p. 13065 - 13072
(2019)
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Organophotoredox-Catalyzed Decarboxylative N-Alkylation of Sulfonamides
We developed an organophotoredox-catalyzed reaction for N-alkylation of sulfonamides with aliphatic carboxylic acid-derived redox active esters as alkylating reagents. Under mild and transition metal-free conditions, a series of functionalized N-alkylated sulfonamides were prepared. This protocol also enabled the functionalization of pharmaceutical drugs bearing a sulfonamide or carboxylic acid moiety. This radical-mediated process allowed the assembly of three components including sulfonamides, redox active esters, and alkenes to yield complex sulfonamides in a one-pot manner.
Nakagawa, Masanari,Nagao, Kazunori,Ikeda, Zenichi,Reynolds, Matthew,Ibá?ez, Ignacio,Wang, Junsi,Tokunaga, Norihito,Sasaki, Yusuke,Ohmiya, Hirohisa
p. 3930 - 3933
(2021/08/03)

Zn- And Cu-catalyzed coupling of tertiary alkyl bromides and oxalates to forge challenging C?O, C?S, and C?N bonds
We describe here the facile construction of sterically hindered tertiary alkyl ethers and thioethers via the Zn(OTf)2catalyzed coupling of alcohols/phenols with unactivated tertiary alkyl bromides and the Cu(OTf)2-catalyzed thiolation of unactivated tertiary alkyl oxalates with thiols. The present protocol represents one of the most effective unactivated tertiary C(sp3)? heteroatom bond-forming conditions via readily accessible Lewis acid catalysis that is surprisingly less developed.
Gong, Yuxin,Zhu, Zhaodong,Qian, Qun,Tong, Weiqi,Gong, Hegui
supporting information
p. 1005 - 1010
(2021/02/01)

Facile synthesis of sulfonyl chlorides/bromides from sulfonyl hydrazides
A simple and rapid method for efficient synthesis of sulfonyl chlorides/bromides from sulfonyl hydrazide with NXS (X = Cl or Br) and late-stage conversion to several other functional groups was described. A variety of nucleophiles could be engaged in this transformation, thus permitting the synthesis of complex sulfonamides and sulfonates. In most cases, these reactions are highly selective, simple, and clean, affording products at excellent yields.
Chen, Rongxiang,Xu, Shaohong,Shen, Fumin,Xu, Canran,Wang, Kaikai,Wang, Zhanyong,Liu, Lantao
(2021/09/20)

Copper-Catalyzed Intermolecular Alkynylation and Allylation of Unactivated C(sp3)-H Bonds via Hydrogen Atom Transfer
We describe Cu-catalyzed intermolecular alkynylation and allylation of unactivated C(sp3)-H bonds with singly occupied molecular orbital-philes (SOMO-philes) via hydrogen atom transfer (HAT). Employing N-fluoro-sulfonamide as a HAT reagent, a set of subst
Liang, Lei,Guo, Ge,Li, Chen,Wang, Song-Lin,Wang, Yue-Hui,Guo, Hai-Ming,Niu, Hong-Ying
supporting information
p. 8575 - 8579
(2021/11/13)

Recurrent Approximation of Retention Parameters of N-Substituted p-Toluenesulfonamides in Reversed-Phase High Performance Liquid Chromatography for Revealing the Formation of Their Hydrates
Abstract: Recurrent approximation of retention times in reversed-phase high performance liquid chromatography (RP-HPLC), tR(C + ΔC) = atR(C) + b, where C is the acetonitrile concentration in the eluent, and ΔC is the constant “step” of its variation, for six specially synthesized N-substituted p-toluenesulfonamides confirmed the presence of anomalies previously revealed for some complex polyfunctional organic compounds. The reason for these anomalies is the presence of sulfonamide –SO2–NH fragments in the molecules, which leads to hydration of sorbates in aqueous solutions, or, more precisely, to a change in the ratio of their non-hydrated and hydrated forms because of a shift in the equilibrium Х + Н2О $$ rightleftarrows $$ Х·Н2О (*) as a result of a change in the eluent composition. The same effect is indicated by the strong antibatic dependence of the retention indices RI(C) of all sulfonamides under study; the coefficients dRI/dC vary from –1.9 to –4.0, these values being much higher in magnitude than for compounds that do not form hydrates. Further independent evidence in favor of the transformation of sorbates due to variation of the eluent composition is the dependence of the relative absorbance Arel = A(254)/A(220) on the acetonitrile content in the eluent. This suggests changes in the chemical nature of chromophores in sulfonamide molecules depending on the equilibrium state (*).
Kornilova, T. A.,Nikitina, D. A.,Zenkevich, I. G.
p. 1931 - 1941
(2021/09/15)

Copper iodide nanoparticles-decorated porous polysulfonamide gel: As effective catalyst for decarboxylative synthesis of N-Arylsulfonamides
A porous cross-linked poly (ethyleneamine)-polysulfonamide (PEA-PSA) as a novel organic support system is synthesized in the presence of silica template by nanocasting technique. The paper demonstrates immobilization of CuI nanoparticles inside the pores (PEA-PSA?CuI) for the facile recovery and recycling of these nanoparticles. The presence of porous PEA-PSA and PEA-PSA?CuI nanocomposites was confirmed using FT-IR spectroscopy, FE-SEM, EDX, TGA, XRD, TEM, BET, XPS, WDX, 1H NMR, and ICP-OES techniques. The PEA-PSA?CuI along with Ag(I)/K2S2O8 was implemented as a reusable cooperative catalyst-oxidant system in the N-arylation of p-toluenesulfonamide with substituted carboxylic acids in mild condition. So, the novel decarboxylative cross-coupling catalyzed by copper and silver has been developed. Aromatic, secondary and tertiary aliphatic acids underwent high efficient decarboxylative processes with p-toluenesulfonamide to afford the corresponding products. This method provides a practical approach for the flexible synthesis of sulfonamides from the readily affordable substrates. The catalyst is highly reusable and efficient, especially in terms of time and yield of the desired product.
Alavinia, Sedigheh,Ghorbani-Vaghei, Ramin,Rakhtshah, Jamshid,Yousefi Seyf, Jaber,Ali Arabian, Iman
(2020/01/22)

COMPOUNDS AND COMPOSITIONS FOR TREATING CONDITIONS ASSOCIATED WITH NLRP ACTIVITY
In one aspect, compounds of Formula AA, or a pharmaceutically acceptable salt thereof, are featured or a pharmaceutically acceptable salt thereof, wherein the variables shown in Formula A can be as defined anywhere herein.
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(2020/06/05)

Synthesis of chiral a-substituted a-amino acid and amine derivatives through Ni-catalyzed asymmetric hydrogenation
Highly efficient Ni-catalyzed asymmetric hydrogenation of cyclicN-sulfonyl ketimino esters was, for the first time, successfully developed, providing various chiral a-monosubstituted a-amino acid derivatives with excellent results (97-99% yields, 90 to >99% ee). CyclicN-sulfonyl ketimines were also hydrogenated well to afford chiral amine derivatives with 98-99% yields and 97 to >99% ee. The gram-scale asymmetric hydrogenation was performed well with 85% yield and 99% ee using only 0.2 mol% catalyst.
Cong, Hengjiang,Dong, Xiu-Qin,Liu, Gongyi,Wang, Heng,Zhang, Xianghe,Zhang, Xumu
supporting information
p. 4934 - 4937
(2020/05/13)

Stereoinversion of Unactivated Alcohols by Tethered Sulfonamides
The direct, catalytic substitution of unactivated alcohols remains an undeveloped area of organic synthesis. Moreover, catalytic activation of this difficult electrophile with predictable stereo-outcomes presents an even more formidable challenge. Described herein is a simple iron-based catalyst system which provides the mild, direct conversion of secondary and tertiary alcohols to sulfonamides. Starting from enantioenriched alcohols, the intramolecular variant proceeds with stereoinversion to produce enantioenriched 2- and 2,2-subsituted pyrrolidines and indolines, without prior derivatization of the alcohol or solvolytic conditions.
Marcyk, Paul T.,Jefferies, Latisha R.,AbuSalim, Deyaa I.,Pink, Maren,Baik, Mu-Hyun,Cook, Silas P.
supporting information
p. 1727 - 1731
(2019/01/21)

Synthesis, Characterization, and Reactivity of an Ethynyl Benziodoxolone (EBX)-Acetonitrile Complex
The synthesis of a crystalline ethynyl-1,2-benziodoxol-3(1H)-one (EBX)-acetonitrile complex is described. EBX has been widely used as an active species for a variety of reactions; however, its high instability has so far prevented its isolation. The EBX-acetonitrile is self-assembled into a double-layered honeycomb structure through weak hypervalent iodine secondary interactions and hydrogen bonding. The N-ethynylation of a variety of sulfonamides using the EBX-acetonitrile complex as a substrate under mild conditions is also described.
Yudasaka, Masaharu,Shimbo, Daisuke,Maruyama, Toshifumi,Tada, Norihiro,Itoh, Akichika
supporting information
p. 1098 - 1102
(2019/05/16)

Highly Enantioselective Synthesis of Fused Tri- and Tetrasubstituted Aziridines: aza-Darzens Reaction of Cyclic Imines with α-Halogenated Ketones Catalyzed by Bifunctional Phosphonium Salt
The first enantioselective aza-Darzens reaction of cyclic imines with α-halogenated ketones was realized under mild reaction conditions by using amino-acid-derived bifunctional phosphonium salts as phase-transfer promoters. A variety of structurally dense tri- and tetrasubstituted aziridine derivatives, containing benzofused heterocycles as well as spiro-structures, were readily synthesized in high yields with excellent diastereo- and enantioselectivities (up to >20:1 d.r. and >99.9 % ee). The highly functionalized aziridine products could be easily transformed into different classes of biologically active compounds.
Pan, Jianke,Wu, Jia-Hong,Zhang, Hongkui,Ren, Xiaoyu,Tan, Jian-Ping,Zhu, Lixiang,Zhang, Hong-Su,Jiang, Chunhui,Wang, Tianli
supporting information
p. 7425 - 7430
(2019/05/10)

Efficient N-acylation of sulfonamides using cesium salt of Wells–Dawson heteropolyacid as catalyst: Synthesis of new N-acyl sulfonamides and cyclic imides
N-acylation of substituted sulfonamides with different anhydrides in the presence of Cesium salt of Wells–Dawson heteropolyacid (Cs5HP2W18O62) as an efficient and reusable catalyst was investigated for the first time. ?Cs5HP2W18O62 was used with a catalytic amount in water as a green solvent. At room temperature, a series of N-acylsulfonamides were synthesized, while under refluxing conditions, new cyclic imides containing sulfonyl group were obtained. Atom-economy, high yields, easy work-up, as well as simple catalyst recovery and reusability are the key features of this procedure.
Benali, Nesma,Bougheloum, Chafika,Alioua, Sabrina,Belghiche, Robila,Messalhi, Abdelrani
p. 3099 - 3112
(2018/12/04)

Three-Component Ring-Opening Reactions of Cyclic Ethers, α-Diazo Esters, and Weak Nucleophiles under Metal-Free Conditions
A protocol for three-component reactions of cyclic ethers, α-diazo esters, and weak nitrogen, oxygen, carbon, and sulfur nucleophiles (pKa = 2.2-14.8) to afford a variety of structurally complex α-oxyalkylated esters is reported. These reactions involve intermolecular activation of the cyclic ether (present in excess) by the α-diazo ester to form an oxonium ylide under metal-free conditions, followed by ring opening by the nucleophile.
Lu, Lin,Chen, Chuwei,Jiang, Huanfeng,Yin, Biaolin
p. 14385 - 14395
(2018/11/27)

Cobalt-Catalyzed Asymmetric Allylation of Cyclic Ketimines
A CoII/Box-catalyzed [Box=bis(oxazoline)] enantioselective addition of potassium allyltrifluoroborate to cyclic ketimines was developed, providing the corresponding chiral α-tertiary amines in high yields and with good enantioselectivity values. Alkoxycarbonyl- and alkyl-substituted saccharin-derived ketimines are suitable substrates for this allylation reaction. The product can be converted to complex molecules over several simple steps, including a precursor of MK-0371, which is a kinesin spindle protein inhibitor. In addition, this catalytic system showed a strong positive nonlinear effect.
Wu, Liang,Shao, Qihang,Yang, Guoqiang,Zhang, Wanbin
supporting information
p. 1241 - 1245
(2017/12/15)

Copper (II)/RuPHOX-Catalyzed Enantioselective Mannich-Type Reaction of Glycine Schiff Bases with Cyclic Ketimines
A Cu(II)/RuPHOX-catalyzed enantioselective Mannich-type reaction of glycine Schiff bases with cyclic ketimines was developed, affording chiral α,?-diamino acid derivatives in good yields with moderate to good ee and dr values. This provides an efficient methodology for furnishing chiral Cβ-tetrasubstituted α,β-diamino acid precursors. The catalytic system is compatible with a series of substrates. In addition, an interesting nonlinear effect of the catalyst's enantiomeric composition on reaction enantioselectivity was observed. (Figure presented.).
Shao, Qihang,Wu, Liang,Chen, Jianzhong,Gridnev, Ilya D.,Yang, Guoqiang,Xie, Fang,Zhang, Wanbin
supporting information
p. 4625 - 4633
(2018/11/10)

Synthesis of 2-(p-toluenesulphonyl) tropane-2-ene: Anhydroecgonine analog
The present work is intended to provide a process for synthesizing anhydroecgonine derivatives without using cocaine as a starting material. This process involves the synthesis of an anhydroecgonine bearing sulphonyl group instead of carboxylate group at the position C2for the tropane system, from 7-(p-toluenesulphonyl)cyclohepta-2,4,6-triene and a variety of amines.
Alsamarrai, Abdulmajeed Salih Hamad
p. 252 - 254
(2017/01/22)

Direct Sulfonamidation of Primary and Secondary Benzylic Alcohols Catalyzed by a Boronic Acid/Oxalic Acid System
The direct sulfonamidation of primary and secondary benzylic alcohols catalyzed by a 2,3,4,5-tetrafluorophenylboronic acid/oxalic acid co-catalytic system was examined. The reaction proceeds under mild conditions with readily available starting materials and has been shown to be gram-scalable without significant decrease of yield. Both primary and secondary benzylic alcohols were evaluated and afforded the desired sulfonamide products with good to excellent yields.
Verdelet, Tristan,Ward, Robert M.,Hall, Dennis G.
p. 5729 - 5738
(2017/10/06)

Targeted Polypharmacology: Discovery of a Highly Potent Non-Hydroxamate Dual Matrix Metalloproteinase (MMP)-10/-13 Inhibitor
Matrix metalloproteinases (MMPs) play a key role in many diseases like cancer, atherosclerosis or arthritis. Interest in MMP inhibition has been revitalized very recently as the knowledge on the underlying network of biological pathways is steadily growing. On the basis of this new insight into the relevance of MMP-10 and MMP-13 within the MMP network and the ban of hydroxamate inhibitors from clinical development, the discovery of non-hydroxamate multitarget drugs against specific MMPs is of foremost interest. Here, we disclose the discovery of a very potent and selective non-hydroxamate MMP-10/-13 inhibitor. The high potency (IC50 of 31 nM [MMP-10] and 5 nM [MMP-13]) and selectivity over MMP-1, -2, -3, -7, -8, -9, -12, and -14 enable this compound to decipher disease causing MMP networks and to generate new treatment options through targeted polypharmacology.
Senn, Nicole,Ott, Michael,Lanz, Jan,Riedl, Rainer
p. 9585 - 9598
(2017/12/26)

Copper-catalyzed asymmetric alkynylation of cyclic: N -sulfonyl ketimines
A Cu-catalyzed asymmetric alkynylation of cyclic N-sulfonyl ketimines was developed, providing the corresponding chiral α-tertiary amines with up to 98% ee. The method tolerates some variations in cyclic N-sulfonyl ketimine and alkyne scope. These products could be used in several transformations, in particular, the products of 6-membered cyclic N-sulfonyl ketimines could be easily converted to linear chiral α-tertiary amines. This asymmetric alkynylation provides an efficient, gram-scale, low-cost transition-metal catalyzed synthesis of chiral α-tetrasubstituted propargylamines.
Ling, Zheng,Singh, Sonia,Xie, Fang,Wu, Liang,Zhang, Wanbin
supporting information
p. 5364 - 5367
(2017/07/06)

A synthetic method of the compound benzenesulfonyl amine
The invention relates to a method for preparing benzene sulfonamide compounds. In the method, a ternary catalyzing system of ethyltriphenylphosphonium bromide-silver compounds-porphyrin is adopted; the method for preparing N-tert-Butylbenzenesulfenamide from the reaction of methyl tertiary butyl ether with a weak reactivity and benzene sulfonamide compounds is realized; remarkably technical effects of preferable reaction temperature, high yield and good universality are achieved; moreover, as appropriate additives are added in the reaction, the collision between molecules is promoted and the reaction time is shortened; the method has favorable industrialization perspective and industrialized production value.
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Paragraph 0043; 0044; 0045

(2017/03/08)

Visible-light-mediated, nitrogen-centered radical amination of tertiary alkyl halides under metal-free conditions to form α-tertiary amines
A mild and operationally convenient amino-functionalization of a range of tertiary alkyl halides by reaction with iminoiodinanes (PhINNs) and I2 has been developed. According to the mechanistic experiments described within, the reaction is spec
Brueckner, Alexander C.,Hancock, Erin N.,Anders, Evan J.,Tierney, Matthew M.,Morgan, Heather R.,Scott, Kristina A.,Lamar, Angus A.
supporting information
p. 4387 - 4392
(2016/06/06)

Metal-free synthesis of sulfonamides via iodine-catalyzed oxidative coupling of sulfonyl hydrazides and amines
A novel, rapid, and environmentally-friendly protocol for the synthesis of sulfonamides using iodine as catalyst under solvent-free conditions is described. This method involves the oxidative coupling of sulfonyl hydrazides and amines in the presence of catalytic amount of iodine using TBHP as oxidant. This protocol does not require purification techniques such as column chromatography and recrystalization.
Parumala, Santosh Kumar Reddy,Peddinti, Rama Krishna
supporting information
p. 1232 - 1235
(2016/03/01)

Electrosynthesis of Arylsulfonamides from Amines and Sodium Sulfinates Using H2O-NaI as the Electrolyte Solution at Room Temperature
With H2O as the solvent and NaI as the supporting electrolyte, a green and efficient electrochemical route has been developed to synthesize arylsulfonamides via I2electrogenerated in situ at a graphite anode to promote the reaction of sodium sulfinates with aromatic or aliphatic primary and secondary amines. The target products could be obtained in good to excellent yields at room temperature.
Zhang, Chen,Chen, Yibin,Yuan, Gaoqing
p. 1277 - 1282
(2016/12/27)

The mechanism of alkene elimination from protonated toluenesulphonamides generated by electrospray ionisation
The positive ion electrospray mass spectra of a range of sulphonamides of general structure CH3C6H4SO2NHR1 [R1 = CnH2n+1 (n = 1-7), CnH2n-1 (n = 3, 4), C6H5, C6H5CH2 and C6H5CH(CH3)] and CH3C6H4SO2NR1R2 [R1, R2 = CnH2n+1 (n = 1-8)] are reported and discussed. The protonated sulphonamides derived from saturated primary and secondary aliphatic amines generally fragment to only a limited extent unless energised by collision. Two general fragmentations are observed: firstly, elimination of an alkene, CnH2n, obtained by hydrogen abstraction from one of the CnH2n+1 alkyl groups on nitrogen; secondly, cleavage to form CH3C6H4SO2+. The mechanism by which an alkene is lost has been probed by studying the variation of the intensity of the [M + H - CnH2n]+ signal with the structure of the alkyl substituent(s) on nitrogen and by monitoring the competition between the loss of different alkenes from protonated unsymmetrical sulphonamides in which two different alkyl groups are attached to nitrogen. This fragmentation is favoured by branching of the alkyl group at the carbon atom directly attached to nitrogen, thus suggesting that it involves a mechanism in which the stability of the cation obtained by stretching the bond connecting the nitrogen atom to the alkyl group is critical. This interpretation also explains the competition between alkene elimination and cleavage to form CH3C6H4SO2+ (and, in some cases, cleavage to form C6H5CH2+ or [C6H5CHCH3]+).
Saidykhan, Amie,Ebert, Jenessa,Martin, William H.C.,Gallagher, Richard T.,Bowen, Richard D.
p. 165 - 173
(2016/11/09)

Iodine-catalyzed expeditious synthesis of sulfonamides from sulfonyl hydrazides and amines
A new synthesis of sulfonamides has been developed via an iodine-catalyzed sulfonylation of amines with arylsulfonyl hydrazides. This metal-free strategy employs readily accessible and easy to handle starting materials, catalysts and oxidants, and can be easily conducted under mild conditions, providing a convenient access to a wide range of sulfonamides in moderate to excellent yields within a short reaction time.
Yotphan, Sirilata,Sumunnee, Ladawan,Beukeaw, Danupat,Buathongjan, Chonchanok,Reutrakul, Vichai
p. 590 - 597
(2016/01/12)

Iodine-catalyzed oxidative amination of sodium sulfinates: A convenient approach to the synthesis of sulfonamides under mild conditions
The iodine-catalyzed oxidative amination of sodium sulfinates in the presence of sodium percarbonate as the oxidant has been developed. The reaction shows good substrate scope and tolerates a wide range of functionalities in both amine and sodium sulfinate substrates. Aliphatic amines, heteroaromatic amines and hydrochloride salts of amines canbe employed as the amine sources in this transformation. Mechanistic studies indicated that a radical pathway might be involved in the reaction process. This transition-metalfree protocol offers an alternative and convenient approach for a preparation of a series of sulfonamides in moderate to good yields under mild conditions.
Buathongjan, Chonchanok,Beukeaw, Danupat,Yotphan, Sirilata
p. 1575 - 1582
(2015/03/04)

Synthesis of sulfonamides via I2-mediated reaction of sodium sulfinates with amines in an aqueous medium at room temperature
An efficient I2-mediated approach for the synthesis of sulfonamides at room temperature using water as the solvent has been developed. This method for the synthesis of sulfonamides is quite convenient and environmentally friendly. In addition, the purification procedure of the desired products becomes very easy. This journal is
Pan, Xiaojun,Gao, Jian,Liu, Juan,Lai, Junyi,Jiang, Huanfeng,Yuan, Gaoqing
supporting information
p. 1400 - 1403
(2015/03/18)

Methylprenyl and prenyl protection for sulfonamides
2-Methylprenyl (MePre) is an efficient protection for sulfonamides. The acidic cleavage of this group leads to volatile by-products and the product can be obtained in high purity without additional purification. MePre group is resistant to Pd/C-catalysed hydrogenolysis at 1 atm, Suzuki-Miyaura reaction, Ni(0) catalysis conditions and oxidising reagents such as NIS and DDQ. The prenyl (Pre) group can also be used to protect sulfonamides in certain cases; however, the substrate scope is limited due to the side product formation.
Nikitjuka, Anna,Nekrasova, Aleksandra,Jirgensons, Aigars
supporting information
p. 183 - 186
(2015/03/04)

Tosyl oxygen transfer and ion-neutral complex mediated electron transfer in the gas-phase fragmentation of the protonated N-phenyl p-toluenesulfonamides
In this work, an interesting oxygen transfer reaction in the gas phase dissociation of N-phenyl p-toluenesulfonamides has been explored by combination of the ESI-MS techniques and theoretical calculations. The protonated molecules underwent dissociation reactions, upon collisional activation, to give the [tosyl cation/aniline] ion-neutral complex (INC), in which the coupling reactions subsequently occurred to afford an ionic species of toluenesulfinate. The subsequent reactions of the toluenesulfinate species resulted in generation of the protonated 6-iminocyclohexa- 2,4-dienone or the 2-aminophenol radical cation, via cleavage of the SO bond. The above processes involved the tosyl oxygen transfer, and calculation results indicated that both the ortho- and the para- positions at the aniline ring are favorite for the tosyl oxygen transfer, and formation of radical cation involved an INC mediated electron transfer. The isomeric N-methylphenyl p-toluenesulfonamides behaved significant difference in the CID-MS spectra, indicating that the three isomers can be distinguished by ESI-MS.
Wang, Shanshan,Guo, Cheng,Zhang, Ningwen,Wu, Yanqing,Zhang, Huarong,Jiang, Kezhi
p. 6 - 12
(2015/01/30)

Tosyl oxygen transfer and ion-neutral complex mediated electron transfer in the gas-phase fragmentation of the protonated N-phenyl p-toluenesulfonamides
In this work, an interesting oxygen transfer reaction in the gas phase dissociation of N-phenyl p-toluenesulfonamides has been explored by combination of the ESI-MS techniques and theoretical calculations. The protonated molecules underwent dissociation reactions, upon collisional activation, to give the [tosyl cation/aniline] ion-neutral complex (INC), in which the coupling reactions subsequently occurred to afford an ionic species of toluenesulfinate. The subsequent reactions of the toluenesulfinate species resulted in generation of the protonated 6-iminocyclohexa- 2,4-dienone or the 2-aminophenol radical cation, via cleavage of the SO bond. The above processes involved the tosyl oxygen transfer, and calculation results indicated that both the ortho- and the para- positions at the aniline ring are favorite for the tosyl oxygen transfer, and formation of radical cation involved an INC mediated electron transfer. The isomeric N-methylphenyl p-toluenesulfonamides behaved significant difference in the CID-MS spectra, indicating that the three isomers can be distinguished by ESI-MS.
Wang, Shanshan,Guo, Cheng,Zhang, Ningwen,Wu, Yanqing,Zhang, Huarong,Jiang, Kezhi
p. 6 - 12
(2015/02/19)

Br?nsted acid-assisted N-alkylation of sulfonamides using ethers as the alkylation reagents
N-Alkylation of sulfonamides using cyclic ethers as alkylation reagents and Br?nsted acid as a catalyst produced pyrrolidine and piperidine derivatives in good yields. When using symmetrical and unsymmetrical ethers as alkylation reagents, mono-N-alkylation of sulfonamides took place to afford the corresponding products.
Shi, Wei,Bai, Chun-Mei,Zhu, Kai,Cui, Dong-Mei,Zhang, Chen
p. 434 - 438
(2014/01/06)

Methylprenyl and prenyl protection for sulfonamides
2-Methylprenyl (MePre) is an efficient protection for sulfonamides. The acidic cleavage of this group leads to volatile by-products and the product can be obtained in high purity without additional purification. MePre group is resistant to Pd/C-catalysed hydrogenolysis at 1 atm, Suzuki-Miyaura reaction, Ni(0) catalysis conditions and oxidising reagents such as NIS and DDQ. The prenyl (Pre) group can also be used to protect sulfonamides in certain cases; however, the substrate scope is limited due to the side product formation.
Nikitjuka, Anna,Nekrasova, Aleksandra,Jirgensons, Aigars
(2015/02/02)

Metal-free oxidative coupling of amines with sodium sulfinates: A mild access to sulfonamides
A practical and mild procedure for the preparation of sulfonamides through TBAI-catalyzed oxidative coupling of amines with sodium sulfinates using TBHP as an oxidant was presented. A variety of amines and sodium sulfinates could go through the transformation, without impacting the hydroxyl group. This journal is
Zhao, Jinwu,Xu, Jingxiu,Chen, Jiaxi,Wang, Xiaoqin,He, Minghua
p. 64698 - 64701
(2015/04/27)

Copper-catalyzed sulfonamides formation from sodium sulfinates and amines
A new and convenient method for the construction of sulfonamides via a copper-catalyzed oxidative coupling between sodium sulfinates and amines with 1 atm O2 or DMSO as the oxidant was described. This method provides efficient and robust synthesis of functional sulfonamides in good yields and excellent chemoselectivity. And detailed mechanistic studies showed that this transformation may go through a single electron transfer (SET) pathway.
Tang, Xiaodong,Huang, Liangbin,Qi, Chaorong,Wu, Xia,Wu, Wanqing,Jiang, Huanfeng
supporting information
p. 6102 - 6104
(2013/07/11)

Simple branched sulfur-olefins as chiral ligands for Rh-catalyzed asymmetric arylation of cyclic ketimines: Highly enantioselective construction of tetrasubstituted carbon stereocenters
New, simple, sulfinamide-based branched olefin ligands have been developed and successfully used in Rh-catalyzed asymmetric arylations of cyclic ketimines, providing efficient and highly enantioselective access to valuable benzosultams and benzosulfamidat
Wang, Hui,Jiang, Tao,Xu, Ming-Hua
supporting information
p. 971 - 974
(2013/04/10)

Design, synthesis, and biological evaluation of 1,2,4-triazole bearing 5-substituted biphenyl-2-sulfonamide derivatives as potential antihypertensive candidates
A series of novel 1,2,4-triazole bearing 5-substituted biphenyl-2- sulfonamide derivatives were designed and synthesized to develop new angiotensin II subtype 2 (AT2) receptor agonists as novel antihypertensive candidates. It was found that 14f (IC50 = 0.4 nM) and 15e (IC 50 = 5.0 nM) displayed potent AT2 receptor affinity and selectivity in binding assays. Biological evaluation in vivo suggested that 14f is obviously superior to that of reference drug losartan in RHRs, and meanwhile, 14f has no significant impact on heart rate. The interesting activities of these compounds may make them promising candidates as antihypertensive agents.
Liu, Jie,Liu, Qin,Yang, Xue,Xu, Shengtao,Zhang, Hengyuan,Bai, Renren,Yao, Hequan,Jiang, Jieyun,Shen, Mingqin,Wu, Xiaoming,Xu, Jinyi
p. 7742 - 7751
(2014/01/06)

NAlkylation of tosylamides using esters as primary and tertiary alkyl sources: Mediated by hydrosilanes activated by a ruthenium catalyst
Select your group: Either a primary or tertiary alkyl group can be selectively introduced onto the nitrogen atom of tosylamides in a ruthenium-catalyzed reaction employing hydrosilanes through a judicious choice in the esters that serve as the alkyl source (see scheme; Ts= 4-toluenesulfonyl). These N-alkylation reactions are useful for construction of naturally occurring azacyclic skeletons. Copyright
Nishikata, Takashi,Nagashima, Hideo
supporting information; experimental part
p. 5363 - 5366
(2012/07/03)

Zirconium-catalyzed intermolecular hydroamination of alkynes with primary amines
A simple catalyst system generated in situ by combination of 5 mol-% [Zr(NMe2)4] and 10 mol-% of a sulfonamide catalyzes the intermolecular hydroamination of alkynes with primary amines. At elevated temperatures, hydroamination is achieved with both internal and terminal alkynes as well as with sterically demanding and less demanding primary amines. In contrast, secondary amines do not react under identical conditions. Of the sulfonamide additives investigated, sterically demanding tosylamides such as N-(tert-butyl)-p-toluenesulfonamide give the best results. The regioselectivity of the addition of amine to unsymmetrically substituted internal as well as terminal alkynes is significantly influenced by the nature of the sulfonamide additive. In particular, the successful use of sterically less demanding primary amines such as n-hexyl-or benzylamine clearly indicates that the assumption that Zr catalysts generally form catalytically inactive bridging μ2-imido dimers or other unreactive intermediates in the presence of these amines is not correct. Intermolecular hydroamination reactions of alkynes with primary amines that are sterically less demanding than 2,6-dimethylaniline can be achieved with in situ generated zirconium catalysts. This finding is highly important for a better and more general understanding of the mechanism of group 4 metal-catalyzed hydroamination reactions. Copyright
Born, Karolin,Doye, Sven
supporting information; experimental part
p. 764 - 771
(2012/03/22)

Sultone opening with [18F]fluoride: An efficient 18F-labelling strategy for PET imaging
Sultones were subject to ring opening by nucleophilic attack with [ 18F]fluoride to afford easily purified 18F-labelled hydrophilic sulfonated products in high yields. A two-step sequence including radiofluorination and coupling to l
Schmitt, Sebastien,Bouteiller, Cedric,Barre, Louisa,Perrio, Cecile
supporting information; experimental part
p. 11465 - 11467
(2011/11/13)

Copper-catalyzed formation of sulfur-nitrogen bonds by dehydrocoupling of thiols with amines
Copper-catalyzed formation of sulfur-nitrogen bonds can be performed by a dehydrocoupling of aryl thiols with amines. Sulfenamides or sulfonamides can be produced by the use of a copper catalyst in air or under oxygen atmosphere. Furthermore, a reaction involving the combination of a palladium catalyst and a copper catalyst selectively afforded sulfinamides.
Taniguchi, Nobukazu
experimental part
p. 2670 - 2673
(2010/07/18)

Development of practical syntheses of potent non-nucleoside reverse transcriptase inhibitors
The development of practical and efficient syntheses of the potent non-nucleoside reverse transcriptase inhibitors 1 and 2 is described. The preparation of 1 proceeded in four synthetic steps and in 48% overall yield from 3. The long-term synthesis of 2 proceeded in nine synthetic steps and in 47% overall yield from commercially available 2,6-diflurorpyridine. The route to 2 was highlighted by the three-step synthesis of intermediate 22 and the high yielding coupling between 18 and phenol 8. The overall sequence required no chromatography and has successfully been utilized for the manufacture of 2 on large scale.
Kuethe, Jeffrey T.,Zhong, Yong-Li,Alam, Mahbub,Alorati, Anthony D.,Beutner, Gregory L.,Cai, Dongwei,Fleitz, Fred J.,Gibb, Andrew D.,Kassim, Amude,Linn, Kathleen,Mancheno, Danny,Marcune, Benjamin,Pye, Philip J.,Scott, Jeremy P.,Tellers, David M.,Xiang, Bangping,Yasuda, Nobuyoshi,Yin, Jingjun,Davies, Ian W.
experimental part
p. 5013 - 5023
(2009/11/30)

A simple and efficient method for sulfonylation of amines, alcohols and phenols with cupric oxide under mild conditions
Cupric Oxide efficiently catalyzed the synthesis of sulfonamides and sulfonic esters. This method has been applied to a variety of substrates including nucleophilic and sterically-hindered amines, alcohols and phenols with excellent yields of sulfonamides and sulfonic esters. The remarkable selectivity under mild and neutral conditions of this commercially available inexpensive catalyst is an attractive feature of this method.
Meshram,Patil, Vishvanath D.
scheme or table
p. 1117 - 1121
(2009/05/27)

Trichlorophenol (TCP) sulfonate esters: A selective alternative to pentafluorophenol (PFP) esters and sulfonyl chlorides for the preparation of sulfonamides
2,4,6-Trichlorophenol (TCP) sulfonate esters undergo effective aminolysis under conventional heating and microwave irradiation; the reactivity of these species is such that chemoselective transformations of PFP sulfonate esters can be achieved. The Royal Society of Chemistry.
Wilden, Jonathan D.,Geldeard, Lynsey,Lee, Chieh C.,Judd, Duncan B.,Caddick, Stephen
p. 1074 - 1076
(2007/12/29)

A novel approach for the synthesis of alkyl and aryl sulfonamides
A novel approach for the synthesis of alkyl and aryl sulfonamides by the reaction of sulfonic acids, isocyanides and water in dichloromethane is reported at ambient temperature in excellent yields within 20 min. To the best of our knowledge this is the first report on the synthesis of this biologically important family using easily available sulfonic acids and isocyanides.
Shaabani, Ahmad,Soleimani, Ebrahim,Hossein Rezayan, Ali
p. 2185 - 2188
(2008/02/04)

A general and efficient 2-amination of pyridines and quinolines
(Chemical Equation Presented) Pyridine N-oxides were converted to 2-aminopyridines in a one-pot fashion using Ts2O-t-BuNH2 followed by in situ deprotection with TFA. The amination proceeded in high yields, excellent 2-/4-selectivity, and with good functional group compatibility. 2-Amino (iso)quinolines were also obtained in the same manner. Combined with the simple oxidation of pyridines to pyridine N-oxides, this method provides a general and efficient way for amination of 2-unsubstituted pyridines.
Yin, Jingjun,Xiang, Bangping,Huffman, Mark A.,Raab, Conrad E.,Davies, Ian W.
p. 4554 - 4557
(2008/02/04)

Mild and efficient indium metal catalyzed synthesis of sulfonamides and sulfonic esters
A facile and efficient method for synthesizing sulfonamides was developed using a catalytic amount of indium metal. A wide range of sulfonamides were synthesized in excellent yields using the new process. The method showed a generality for substrates including less nucleophilic and sterically hindered anilines, and it is also applicable for preparing sulfonic esters from sulfonyl chlorides and alcohols. Georg Thieme Verlag Stuttgart.
Kim, Joong-Gon,Doo, Ok Jang
p. 2501 - 2504
(2008/02/13)

Iodine(III)-Mediated Preparations of Nitrogen-Containing Sulfur Derivatives: Dramatic Influence of the Sulfur Oxidation State
Reaction of sulfonamides with iodosobenzene leads to phenyliodinanes. A new catalysis reaction of the decomposition of these products in the presence of sulfoxides that allows the smooth synthesis of sulfoximines has been evidenced and studied: copper(n) salts were used to prepare compounds 4a-j and 5b, d, f, j, k from the corresponding, easily prepared, sulfoxides. The reactions proceed with retention of configuration at the sulfur center, and copper(II) triflate is the best candidate for the catalyst for the imination. Switching from sulfonamides to sulfinamides in the preparation of the starting iodinanes completely alters the reaction pathway: iodinanes are no longer accessible, and sulfonimidates 7a-j are obtained instead. This behavior can be rationalized by the increase in pKa brought about by the removal of one oxygen atom from the sulfur center. Sulfonimidates are interesting molecules with varied applications. Optimization of their one-pot synthesis has been achieved by carrying out the reaction in acetonitrile. The stereochemical study has shown that the transformation proceeds with global retention of the configuration at the sulfur center, albeit with erosion of the enantiomeric purity. A model accounting for this outcome is proposed. In addition, the presence of oxidized sulfonamide by-products has been explained, and this latter pathway becomes the sole one when alcohol is replaced by water. Good yields of the oxidized products are obtained.
Leca, Dominique,Song, Kai,Amatore, Muriel,Fensterbank, Louis,Lacote, Emmanuel,Malacria, Max
p. 906 - 916
(2007/10/03)

Reactivity of cage-like amines toward p-toluenesulfonyl chloride and diphenyl chlorophosphate in acetonitrile
The nucleophilic reactivity of amines of the norbornane, norbornene, and adamantane series toward p-toluenesulfonyl chloride and diphenyl chlorophosphate in acetonitrile at 25°C is determined mainly by the steric factor. Parameters characterizing spatial accessibility of the reaction center in the amine molecule have been determined. Cage-like substituents show no appreciable effect on the amine reactivity, as compared to common alkyl groups.
Sadovskii,Solomoichenko,Kas'yan,Golodaeva,Anikanova,Kas'yan,Savelova
p. 50 - 56
(2007/10/03)