cas 13636-88-9, 3,3-BIS-METHYLSULFANYL-1-PHENYL-PROPENONE

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Stereochemistry controlled by an asymmetric sulfur atom, and a rare example of a kryptoracemate
The ligands 4-methylthio-6-phenyl-2,2′-bipyridine (1) and the corresponding sulfoxide (2) and sulfone (3) have been synthesized and characterized in solution, and in the solid state by single crystal X-ray diffraction. Compounds 2 and 3 crystallize in the same space group (C2/c) with similar unit cell parameters; a small increase in the unit cell volume allows for the presence of the extra oxygen atom in 3. The sulfoxide and sulfone groups adopt conformations that permit intramolecular O...HCaryl hydrogen bonds. The complexes [Ir(ppy)2L][PF6] with L = 1, 2 or 3 have been prepared and characterized. The asymmetric sulfur atom in ligand 2 gives rise to pairs of diastereoisomers of the complex which can be distinguished in the 1H and 13C NMR spectra. In solution, exchange of [PF6]- by [Δ-TRISPHAT]- gives rise to four diastereoisomers and we observed good dispersion of 1H NMR resonances, especially for those assigned to protons close to the asymmetric sulfur atom. A single crystal X-ray diffraction study of 2{[Ir(ppy) 2(3)][PF6]}·CHCl3·3H 2O reveals that the complex crystallizes in the chiral space group P212121, the asymmetric unit containing crystallographically independent Δ- and Λ-[Ir(ppy) 2(3)]+ cations. This provides a rare example of a so-called kryptoracemate in the solid state. In MeCN solution, [Ir(ppy) 2(1)][PF6], [Ir(ppy)2(2)][PF6] and [Ir(ppy)2(3)][PF6] are weakly emissive (λem = 600, 647 and 672 nm, respectively) and preliminary studies of the electroluminescent properties of [Ir(ppy)2(2)][PF 6] indicate that the complexes are not suitable candidates for LECs.
Bouamaied, Imenne,Constable, Edwin C.,Housecroft, Catherine E.,Neuburger, Markus,Zampese, Jennifer A.
p. 10276 - 10285
(2012)
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Bronsted acid catalyzed PhSe transfer versus radical aryl transfer: Linear codimerization of styrenes and internal olefins
Bronsted acid p-TsOH·H2O-catalyzed hydrovinylation of styrenes with internal olefins α-oxo ketene dithioacetals was efficiently achieved in the presence of N-phenylselenophthalimide (N-PSP), regioselectively affording Markovnikov phenylselenati
Wu, Ping,Wang, Liandi,Wu, Kaikai,Yu, Zhengkun
p. 868 - 871
(2015)
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Evaluation of [12C/11C]carbon monoxide binding to copper(I) tris(pyrazolyl)borate complexes
The copper(I) coordination chemistry of tris(3-R-5-R′-pyrazolyl) borate ligands (TpR,R′) bearing substituent groups attached to the pyrazole rings has been investigated under nitrogen and carbon monoxide atmospheres [1 (TpPh,SMe) R =
Kealey, Steven,White, Andrew J.P.,Gee, Antony D.,Long, Nicholas J.
p. 1896 - 1905
(2014)
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One-Pot Mitsunobu Protocol to Access Ketene S,S-/N,S-Acetals at Room Temperature
With unique chemical reactivity, α-oxoketene S,S- and N,S-acetals have attracted enormous attention in the past decades, whereas limited reports exist for their synthesis via eco-compatible protocols. Herein, we developed a one-pot protocol for symmetrical and unsymmetrical α-oxoketene S,S-/N,S-acetals through chemoselective alkylation of α-enolic dithioesters using Mitsunobu chemistry at room temperature. The operationally simple and user-friendly mild protocol tolerates a wide range of alcohols and α-enolic dithioesters/β-ketothioamides. Short reaction time, good yields, highly selective C?S functionalization, and E/Z-stereoselectivity are imperative characteristics of this strategy.
Saha, Priya,Ansari, Monish Arbaz,Shukla, Gaurav,Singh, Maya Shankar
supporting information
p. 5884 - 5888
(2021/11/27)

Palladium-Catalyzed Fluoroalkylation via C(sp3)-S Bond Cleavage of Vinylsulfonium Salts
An interrupted Pummerer/palladium-catalyzed fluoro-alkylation strategy was developed for alkenyl C-H fluoroalkylthiolation. Palladium-catalyzed ring-opening fluoroalkylation via aliphatic C-S bond cleavage of the vinylsulfonium salts efficiently afforded
He, Yuan,Huang, Zilong,Ma, Juan,Huang, Fei,Lin, Jie,Wang, Hongmei,Xu, Bao-Hua,Zhou, Yong-Gui,Yu, Zhengkun
supporting information
p. 6110 - 6114
(2021/08/03)

Pyrimido-pyrrolopyridazine derivative as well as intermediate, preparation method, pharmaceutical composition and application
The invention discloses a pyrimido-pyrrolopyridazine derivative as well as an intermediate, a preparation method, a pharmaceutical composition and application thereof. The preparation method of the pyrimido-pyrrolopyridazine derivative of a formula I shown in the description comprises the following step: in a solvent, under the action of additives, performing a reaction shown in the description onthe compound of a formula IV shown in the description. By adopting the preparation method disclosed by the invention, defects such as multi-step synthesis and low separation yields in a traditional method can be overcome, and various novel heterocyclic compounds with important biological activity can be rapidly synthesized. The pyrimido-pyrrolopyridazine derivative disclosed by the invention hasgood activity of inhibiting production of NO by macrophage RAW264.7.
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Paragraph 0086-0090

(2020/02/17)

Transition metal free synthesis of multifunctional thiomethylated-benzenes from aryl/heteroaryl/cyclopropyl methyl ketones
A base-promoted strategic synthesis of various functionalized thiomethylated-benzenes has been established from aryl/heteroaryl/cyclopropyl methyl ketone. We can directly access the thiomethylated-benzene nucleus embedded with diverse functional group by
Panwar, Rahul,Althagafi, Ismail,Shally,Shaw, Ranjay,Elagamy, Amr,Shah, Chandan,Yadav, Pratik,Pratap, Ramendra
(2020/04/28)

A [5 + 1] annulation strategy for the synthesis of multifunctional biaryls and: P -teraryls from 1,6-Michael acceptor ketene dithioacetals
A new type of ketene dithioacetal, 2-(3,3-bis-methylsulfanyl-1-arylallylidene)malononitriles containing 1,4 and 1,6-Michael acceptors, were synthesized to study their reactivity for the synthesis of a new molecular entity. We report a [5 + 1] annulation s
Althagafi, Ismail,Elagamy, Amr,Kumar, Abhinav,Pratap, Ramendra,Shally,Shaw, Ranjay
p. 6407 - 6417
(2020/09/07)

Alternative Palladium-Catalyzed Vinylic C?H Difluoroalkylation of Ketene Dithioacetals Using Bromodifluoroacetate Derivatives
A palladium-catalyzed cross-coupling of α-oxo ketene dithioacetals and bromodifluoroacetate derivatives has been developed for the synthesis of a class of CF2-containing tetra-substituted olefins, which has potential to extend to drug design an
Tian, Shuangquan,Song, Xiaoning,Zhu, Dongsheng,Wang, Mang
supporting information
p. 1414 - 1419
(2018/04/10)

Synthesis of Partially Reduced Imidazo[1,2- a ]pyridines through an Unprecedented Base-Mediated (4+2) Cyclization
A water-mediated regioselective synthesis of 6,7-diaryl-5-oxo-2,3,5,6-tetrahydroimidazo[1,2-a]pyridine-6-carbonitriles was performed by the reaction of 2-[1-cyano-2,2-bis(methylsulfanyl)vinyl]benzonitrile with 1-aryl-2-(imidazolidin-2-ylidene)ethanones un
Panwar, Rahul,Singh, Surjeet,Yadav, Pratik,Shaw, Ranjay,Kumar, Abhinav,Pratap, Ramendra
p. 819 - 824
(2017/04/06)

Synthesis and molecular docking studies of novel 2-(2-amino-6-phenyl-4-pyrimidinylamino) ethanol derivatives: Using ring-opening reactions of cyclic ketene-N,O-acetal
A series of six novel 2-(2-amino-6-phenyl-4-pyrimidinylamino) ethanol derivatives have been synthesized starting from commercially available substituted acetophenones via Oxoketene Dithioacetals with high yields. Ketene dithioacetal store act with 2-amino
Kumar, G.M.V.N.A.R. Ravi,Thangamani, Arumugam
p. 1555 - 1562
(2017/07/18)

DBSA-catalyzed hydrolysis of chain α-oxo ketene dithioacetals in water: Aqueous synthesis of β-ketothioesters
In this paper, we wish to report an environment friendly synthetic method for β-ketothioesters from a dodecylbenzenesulfonic acid (DBSA)-catalyzed hydrolysis reaction of chain α-oxo ketene dithioacetals in water. It was shown that the hydrolysis reaction of chain α-oxo ketene dithioacetals could efficiently occur in the presence of 7.5 mol% DBSA at 100 °C in water, affording the desired β-keto thioesters in excellent yields.
Qi, Fei,Yu, Hai-Feng,Wang, Yue-Nan,Lv, Ye,Li, Ya-Xi,Han, Lu,Wang, Rong,Feng, Xi-Ning
supporting information
p. 2220 - 2224
(2017/11/15)

Synthesis of β-amino-α,β-unsaturated ketone derivatives via sequential rhodium-catalyzed sulfur ylide formation/rearrangement
In the presence of a Rh(II) catalyst and β-(methylthio)-α,β-unsaturated ketones, 1-sulfonyl-1,2,3-triazoles can be converted into functionalized β-amino-α,β-unsaturated ketones via formation of α-imino rhodium carbene/sulfur ylide and subsequent rearrangement. The products decompose to useful 2-methylthiopyrrole derivatives conveniently in high yield.
He, Jun,Man, Zengming,Shi, Yinping,Li, Chuan-Ying
p. 4816 - 4823
(2015/05/13)

Synthesis and anti-HCV determinant motif identification in pyranone carboxamide scaffold
Hepatitis C Virus exhibits high genetic diversity. The current treatment for genotype-1 with ～80% sustained virologic responses is a combination of pegylated interferon, ribavirin and boceprevir/telaprevir/simeprevir which is associated with several side
Balaraju, Tuniki,Konreddy, Ananda Kumar,Parveen, Afsana,Toyama, Massaki,Ito, Wataru,Karampuri, Srinivas,Baba, Masanori,Sharon, Ashoke,Bal, Chandralata
supporting information
p. 5224 - 5227
(2015/11/09)

SMALL MOLECULE INHIBITORS OF G PROTEIN COUPLED RECEPTOR 6 KINASES POLYPEPTIDES
This document relates to inhibitors of G protein coupled receptor 6 kinase (GRK6) polypeptides as well as methods and materials for using such inhibitors to treat hematological malignancies, inflammation diseases, and autoimmune disorders.
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Page/Page column 116

(2015/11/16)

Copper-catalyzed trifluoromethylation of internal olefinic C-H bonds: Efficient routes to trifluoromethylated tetrasubstituted olefins and N-heterocycles
The functionalization of internal olefins has been a challenging task in organic synthesis. Efficient CuII-catalyzed trifluoromethylation of internal olefins, that is, α-oxoketene dithioacetals, has been achieved by using Cu(OH)2 as a catalyst and TMSCF3 as a trifluoromethylating reagent. The push-pull effect from the polarized olefin substrates facilitates the internal olefinic C-H trifluoromethylation. Cyclic and acyclic dithioalkyl α-oxoketene acetals were used as the substrates and various substituents were tolerated. The internal olefinic C-H bond cleavage was not involved in the rate-determining step, and a mechanism that involves radicals is proposed based on a TEMPO-quenching experiment of the trifluoromethylation reaction. Further derivatization of the resultant CF 3 olefins led to multifunctionalized tetrasubstituted CF3 olefins and trifluoromethylated N-heterocycles.
Mao, Zhifeng,Huang, Fei,Yu, Haifeng,Chen, Jiping,Yu, Zhengkun,Xu, Zhaoqing
supporting information
p. 3439 - 3445
(2014/04/03)

Synthesis and anti-HCV activity of 4-hydroxyamino α-pyranone carboxamide analogues
High genetic variability in hepatitis C virus (HCV), emergence of drug resistant viruses and side effects demand the requirement for development of new scaffolds to show an alternate mechanism. Herein, we report discovery of new scaffold I based on 4-hydr
Konreddy, Ananda Kumar,Toyama, Massaki,Ito, Wataru,Bal, Chandralata,Baba, Masanori,Sharon, Ashoke
supporting information
p. 259 - 263
(2014/04/03)

Base mediated synthesis of α-aminated aroyl/acetylnaphthalenes through [4+2] annulations
We have developed a base promoted simple, efficient and alternative approach for the synthesis of 4-amino-3-aroyl//heteroaroyl/acetyl-2-methylsulfanyl-naphthalene-1-carbonitriles by reaction of easily accessible 3,3-bis(methylthio)-1-aryl/heteroaryl/acety
Singh, Surjeet,Althagafi, Ismail,Yadav, Pratik,Panwar, Rahul,Kumar, Abhinav,Pratap, Ramendra
p. 8879 - 8884
(2015/03/05)

A convenient base-mediated synthesis of 3-aryol-4-methyl (or benzyl)-2-methylthio furans from α-oxo ketene dithioacetals and propargyl alcohols via domino coupling/annulations
A convenient base-mediated strategy to synthesize 3-aryol-4-methyl (or benzyl)-2-methylthio furans 2 (trisubstituted furans) has been developed through the domino coupling/annulations between available α-oxo ketene dithioacetals 1 and propargyl alcohols.
Yang, Xiaobing,Hu, Fangzhong,Di, Hongjing,Cheng, Xinxin,Li, Dan,Kan, Xiaoli,Zou, Xiaomao,Zhang, Qichun
supporting information
p. 8947 - 8951
(2014/12/11)

Synthesis of densely substituted 1,3-butadienes through acid-catalyzed alkenylations of α-oxoketene dithioacetals with aldehydes
Aldehydes were proved to be viable reagents for implementing alkenylation of α-oxoketene dithioacetals. AlCl3 was found to be the best catalyst. The established reaction opened an avenue to access densely substituted 1,3-butadiene derivatives. The obtained product bears multiple reactive sites that can be converted into various valuable molecules. (Chemical Equation Presented).
Liu, Changhui,Gu, Yanlong
supporting information
p. 9619 - 9627
(2015/01/09)

One-pot straightforward approach to 2,3-disubstituted benzo/naphtho[b] furans via domino annulation of α-oxoketene dithioacetals and 1,4-benzo/naphthoquinone mediated by AlCl3 at room temperature
A versatile and convenient one-pot direct approach to 2,3-disubstituted benzo/naphtho[b]furans via domino annulation of α-oxoketene dithioacetals and 1,4-benzo/naphthoquinone has been achieved in the presence of aluminium chloride at room temperature. Thi
Verma, Girijesh Kumar,Verma, Rajiv Kumar,Shukla, Gaurav,Anugula, Nagaraju,Srivastava, Abhijeet,Singh, Maya Shankar
p. 6612 - 6619
(2013/07/26)

Regioselective synthesis of 3-(methylthio)phenols by formal [3+3]-cyclocondensations of 3-oxo-bis(methylthio)ketenacetals with 1,3-bis(trimethylsilyloxy)-1,3-butadienes and 1,3-dicarbonyl dianions
The cyclization of 1,3-bis(trimethylsilyloxy)-1,3-butadienes with 3-oxo-bis(methylthio)ketenacetals afforded 3-(methylthio)phenols containing an acyl or ester substituent located at position 2. The cyclization of free 1,3-dicarbonyl dianions with 3-oxo-bi
Lubbe, Mathias,Bendrath, Franziska,Trabhardt, Tiana,Villinger, Alexander,Fischer, Christine,Langer, Peter
p. 5998 - 6007
(2013/07/25)

Three-component synthesis of indanone-fused spirooxindole derivatives
A simple, straightforward and versatile multicomponent protocol for the synthesis of indanone-fused spirooxindole derivatives has been developed. The strategy involves the one-pot three-component reaction of heterocyclic ketene aminals, 1H-indene-1,3(2H)-
Chen, Xue-Bing,Liu, Xi-Ming,Huang, Rong,Yan, Sheng-Jiao,Lin, Jun
supporting information
p. 4607 - 4613
(2013/07/26)

Structure based molecular design, synthesis and biological evaluation of α-pyrone analogs as anti-HSV agent
Several options for treating Herpes Simplex Virus type 1 and type 2 are available. However, non-specific inhibition and drug resistance warrants the discovery of new anti-herpetic compounds with better therapeutic profile or different mode of action. The
Karampuri, Srinivas,Bag, Paromita,Yasmin, Sabina,Chouhan, Devendra Kumar,Bal, Chandralata,Mitra, Debashis,Chattopadhyay, Debprasad,Sharon, Ashoke
p. 6261 - 6266
(2012/10/29)

Tin tetrachloride-catalyzed regiospecific allylic substitution of quinone monoketals: An easy entry to benzofurans and coumestans
A highly regioselective allylic substitution of quinone monoketals with a-oxoketene dithioacetals is achieved under the catalysis of only tin tetrachloride (1 mol%). The advantages of the reaction, including its simplicity, rapidity, low catalyst loading of inexpensive tin tetrachloride, mild conditions and; in particular, the regiospecificity, is proposed to be due to a pseudo-intramolecular process. This new synthetic method provides a facile [3+2] cycloaddition route to benzofurans and is highlighted by the synthesis of coumestans.
Liu, Yingjie,Liu, Jingxin,Wang, Mang,Liu, Jun,Liu, Qun
supporting information
p. 2678 - 2682
(2013/01/15)

Synthesis and reactivity of 3-amino-1H-pyrazolo[4,3-c]pyridin-4(5H)-ones: development of a novel kinase-focussed library
3-Amino-1H-pyrazolo[4,3-c]pyridin-4(5H)-ones represent a potentially attractive heteroaromatic scaffold for drug-discovery chemistry. In particular, the arrangement of hydrogen bond donor and acceptor groups in the bicyclic core can fulfil the requirement
Smyth, Lynette A.,Matthews, Thomas P.,Horton, Peter N.,Hursthouse, Michael B.,Collins, Ian
experimental part
p. 2843 - 2854
(2010/06/14)

One-pot synthesis of polyfunctionalized 4H-chromenes and dihydrocoumarins based on copper(II) bromide-catalyzed C-C coupling of benzylic alcohols with ketene dithioacetals
The synthesis of polyfunctionalized 4Hchromenes 3 and dihydrocoumarins 4 has been developed from the same substrates. Catalyzed by copper(II) bromide (0.3 equiv.), the reactions of the easily available ketene dithioacetals 1 with 2-(hydroxymethyl)phenols 2 lead to 4/7-chromenes 3 in high to excellent yields in dichloromethane solvent, whereas, 3,4-trans-disubstituted dihydrocoumarins 4 are obtained in high yields with high diastereoselectivities by prolonging the reaction time or changing the solvent from dichloromethane to acetonitrile.
Liang, Deqiang,Wang, Mang,Bekturhun, Bahargul,Xiong, Binbin,Liu, Qun
supporting information; experimental part
p. 1593 - 1599
(2010/09/08)

Regioselective synthesis of functionalized 3-(methylthio)phenols by the first formal [3+3] cyclocondensations of 1,3-bis(trimethylsilyloxy)-1,3- butadienes with 1,1-bis(methylthio)-1-en-3-ones
The [3+3] cyclocondensation of 1,3-bis(silyl enol ethers) with 1,1-bis(methylthio)-1-en-3-ones results in the regioselective formation of 3-(methylthio)phenols. The products represent useful synthetic building blocks, which are not readily available by ot
Lubbe, Mathias,Klassen, Renske,Trabhardt, Tiana,Villinger, Alexander,Langer, Peter
scheme or table
p. 2331 - 2333
(2009/04/11)

Synthesis of functionalized allylic sulfoxides and their use in the construction of 2,3,4-trisubstituted furans via a [3 + 2] annulation
(Chemical Equation Presented) A route to 2,3,4-trisubstituted furan derivatives based on a [3 + 2] annulation of functionalized allylic sulfoxides and aldehydes is described. In this strategy, the precursors of allylic sulfoxides 4, allylic sulfides 3, were synthesized via a thiomethylation reaction of an α-EWG ketene-S,S-acetal 1 (EWG: electron-withdrawing group), formaldehyde, and a thiol 2 in high to excellent yields. Allylic sulfoxides 4 were prepared by a highly regioselective oxidation of 3, using m-chloroperoxybenzoic acid as oxidant. Thus, starting from these readily available sulfoxides 4, 2-alkylthio-3,4-disubstituted furans 6 were efficiently constructed via the [3 + 2] annulation reaction of 4 with aldehydes 5 under mild conditions. Further replacement of the 2-alkylthio group of 6 with amines led to the formation of 2-amino-3,4-disubstituted furan derivatives 7.
Fu, Zhenqian,Wang, Mang,Ma, Yuhui,Liu, Qun,Liu, Jun
p. 7625 - 7630
(2008/12/22)

A convenient preparation of 2-aroyl-3,3-bis(alkylsulfanyl)acrylaldehydes and their application in the synthesis of 5-aroyl-2-oxo-1,2-dihydro-2- pyridinecarbonitriles
The reaction of aroylketene dithioacetals 1 with Vilsmeier-Haack reagent, prepared from POCl3 and DMF, under mild conditions gave 2-aroyl-3,3-bis(alkylsulfanyl)acrylaldehydes 2 in excellent yields. Cyclization of 2-[2-aroyl-3,3-bis(methylsulfan
Anabha, Engoor R.,Asokan, Chittoorthekkathil V.
p. 151 - 155
(2007/10/03)

Facile synthesis of 4-alkyl (and aryl)-2-aryl-6-diazo-4H-thieno[3,2-b] pyridine-5,7-diones
Treatment of 3-{3-alkyl (and aryl)amino-5-arylthieno-2-yl}-2-diazo-3- oxopropanoates 8 with TMSOTf (3 equiv) in the presence of Et3N (6 equiv) in CH2Cl2 for 1 h at room temperature afforded 4-alkyl (and aryl)-2-aryl-6-diazo-4H-thieno
Lee, Dong Joon,Kim, Kyongtae
p. 4867 - 4869
(2007/10/03)

1,4-Diazabicyclo[3.2.2]nonane-phenylisoxazole derivatives, preparation and therapeutic use thereof
Compounds corresponding to general formula (I) in which R1, R2, R3, R4 and R5 each represent, independently of one another, a hydrogen or halogen atom or a nitro, amino, trifluoromethyl, trifluoromethoxy, cyano, hydroxy, (C1-C6)alkyl, (C1-C6)alkoxy or phenyl group, it also being possible for two of these substituents in adjacent positions together to represent a methylenedioxy group, and R6 represents a hydrogen atom or a (C1-C6)alkyl group. Application in therapeutics.
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(2008/06/13)

Dianions of 3-oxodithioic acids: Preparation and conversion to 3H-1,2-dithiole-3-thiones
Reaction of ketones with CS2 and 2 equivalents of KH in THF-N,N'-dimethylpropyleneurea solution produces the dianions of 3-oxodithioic acids. These dianions are converted in good yield to 3H-1,2-dithiole-3-thiones by the sequential action of hexamethyldisilathiane and an oxidizing agent such as hexachloroethane. (C) 2000 Elsevier Science Ltd.
Curphey,Libby
p. 6977 - 6980
(2007/10/03)

Synthesis of α-oxoketene O-alkyl/aryl, S-alkyl acetals
The synthesis of acylketene O,S-dialkyl acetals 2a-p and acylketene O-aryl S-alkyl acetals 6a-i is described. The compounds 2a-n are obtained by base-catalyzed alkylation of the respective β-oxo thiono esters 4a-n prepared by alkoxythiocarbonylation of ac
Purkayastha,Chandrasekharam,Vishwakarma,Ila,Junjappa
p. 245 - 249
(2007/10/02)

A convenient one-pot synthesis of ketene dithioacetals
An easy synthesis of ketene dithioacetals 2 and 3 by the condensation of carbon disulfide and active methylene compounds 1 with subsequent alkylation in the presence of potassium fluoride is described.
Villemin,Alloum
p. 301 - 303
(2007/10/02)

Synthesis of γ-Lactones by the Intramolecular Radical Cyclization of 2-Bromo-3,3-bis(methylthio)propionates. A Useful Ketene Radical Synthon
The first example of intramolecular radical cyclization of ketene radical synthon is presented.Intramolecular radical cylization of 2-bromo-ketene-S,S-acetals proceeded highly regioselectively to give the corresponding 5-exo-trig cyclized γ-lactones.
Iwasa, Seiji,Yamamoto, Makoto,Furusawa, Atsuko,Kohmoto, Shigeo,Yamada, Kazutoshi
p. 1457 - 1460
(2007/10/02)

Synthesis of Dimethyl Oxazolidine and Tetrahydro-2H-1,3-oxazine Ring Substituted Ketene N,O-Acetals
Dimethyl oxazolidine and tetrahydro-2H-1,3-oxazine ring substituted ketene N,O-acetals 3 and 4 were synthesized by the reaction of ketene S,S-acetals 2 with the corresponding amino alcohols.
Huang, Zhi-Tang,Zhang, Ping-Cheng
p. 1399 - 1407
(2007/10/02)

Synthesis, Reactions, and Tautomerism of Ketene N,S-Acetals with Benzothiazoline Ring
Ketene dithioacetals 2 react with 2-aminothiophenol to afford the corresponding substituted 2(3H)-methylenebenzothiazoles 3.Some compounds 3 react with α,β-unsaturated esters to give 1H-pyridobenzothiazole derivatives 4 and 5 by an electrophilic addition and cyclocondensation sequence.
Huang, Zhi-Tang,Shi, Xian
p. 541 - 547
(2007/10/02)

SYNTHESIS OF CHIRAL HETEROCYCLIC KETENE N,O-ACETALS
Chiral heterocyclic ketene N,O-acetals 3 were synthesized by the reaction of ketene mercaptals 2 with (R)-(-)-2-amino-1-butanol.
Huang, Zhi-Tang,Zhang, Ping-Cheng
p. 2999 - 3006
(2007/10/02)

Synthesis of Heterocyclic Ketene N,O-Acetals and Their Reactions with α,β-Unsaturated Esters
Ketene dithioacetals 2 react with 2-aminoethanol or 1-amino-2-propanol to afford the corresponding substituted 2-methyleneoxazolidines 3 and 4.In some cases, 3 and 4 react with α,β-unsaturated esters to give 5H-oxazolopyridine derivatives 5 by an e
Huang, Zhi-Tang,Zhang, Ping-Cheng
p. 2011 - 2016
(2007/10/02)

SYNTHESIS OF BENZOYL SUBSTITUTED HETEROCYCLIC KETENE AMINALS BY CONDENSATION OF BENZOYL KETENE MERCAPTALS WITH DIAMINES
2-(Benzoylmethylene)imidazolidines 2 and 5, -hexahydropyrimidines 3 and 6, or -hexahydro-1H-1,3-diazepines 4 were synthesized by the reaction of benzoyl substituted ketene mercaptals 1 with diamines.
Huang, Zhi-tang,Liu, Zhi-rong
p. 943 - 958
(2007/10/02)

EFFICIENT SYNTHESIS OF DITHIOACETALS OF α-OXOKETENE AND DITHIOFULVENES UNDER PHASE TRANSFER CATALYSIS CONDITIONS
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Lakeev, S. I.,Galin, F. Z.,Tolstikov, G. A.
p. 202
(2007/10/02)

A Practical Synthetic Method for β-Ketosters from Ketones
A practical, simple, one-pot synthesis of β-ketoesters (3) from ketones (1) via bis(methylthio)ketene acetals (4) was achieved. Keywords---β-ketoester; bis(methylthio)ketene acetals; C-alkoxycarbonylation; ketone; carbon disulfide
Tomozane, Hideo,Takeuchi, Yasuo,Yamato, Masatoshi
p. 401 - 404
(2007/10/02)

Bromination of α-Aroylketene S,S-Acetals: Synthesis of Novel α-Aroyl-α-bromoketene S,S-Acetals and Their Further Synthetic Transformations
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Singh, Gurdeep,Ila, Hiriyakkanavar,Junjappa, Hiriyakkanavar
p. 165 - 169
(2007/10/02)

Polarized Ketene Dithioacetals. Part 26. Studies on Base-catalysed Rearrangements of 3,3-Bis(alkylthio)-2-methyl-1-arylprop-2-en-1-ones and 3,3-Bis(methylthio)-2-benzyl-1-phenylprop-2-en-1-one
3,3-Bis(alkylthio)-2-methyl-1-arylprop-2-en-1-ones (1a-e) undergo facile rearrangement in the presence of sodium hydride in dimethylformamide to give the corresponding 3-alkylthio-2-alkylthiomethylacrylophenones (2a-e), respectively.Similarly 3,3-bis(methylthio)-2-benzyl-1-phenylprop-2-en-1-one (13) under similar conditions yielded the rearranged product, the chalcone (14) and the acrylophenone (15), in addition to two more products, β-methylthiochalcone (16) and the propenone (17).The mechanisms governing these transformations have been studied and it has been shown that the 1,3-RS shift in the dithioacetal intermediate (19) involves intermolecular participation of thiolate anion rather than a concerted process.A probable mechanism involving the solvent equilibrated enolate anion (27) formed by Michael addition of thiolate anion to (19) or the phenyl derivative (26) has been suggested for the rearrangement of (19) to the products (2) and of (26) to either conpound (14) or (15).Also, the formation of products (16) or (17) is explained through oxidative cleavage of the carbanions (28) and (31) respectively.
Apparao, Satyam,Ila, Hiriyakkanavar,Junjappa, Hirijakkanavar
p. 2837 - 2844
(2007/10/02)

Synthesis of 2,6-Disubstituted Pyridines, Polypyridinyls, and Annulated Pyridines
1,5-Enediones containing a variety of substituents in the 1,5-positions are formed in good yields by the reaction of methyl ketone enolates, generated with potassium tert-butoxide, with α-oxoketene dithioacetals, the latter being prepared from alkyl, cycloalkyl, aryl, or heteryl methyl ketones, NaH, CS2, and CH3I.Ring closure of the 1,5-enediones with NH4OAc gave 2,6-disubstituted 4-(methylthio)pyridines in good to excellent yields.This procedure is particularly suited for the synthesis of 2,6-diheterylpyridines and provides a simple synthesis of terpyridinyl and other oligopyridines.The methylthio groups in the α-oxoketene dithioacetals may be oxidized to the mono- and disulfoxides with m-chloroperbenzoic acid, but with excess peracid, in addition to oxidation to the disulfone, epoxidation of the double bond also occurs.The pyridine 4-methylthio substituent may also be oxidized to the sulfoxide and to the sulfone, and the latter may be displaced with cyanide ion to form the corresponding 4-carbonitrile.
Potts, Kevin T.,Cipullo, Michael J.,Ralli, Philip,Theodoridis, George
p. 3027 - 3038
(2007/10/02)