- A convenient synthesis of N-tert-butyl amides by the reaction of di-tert-butyl dicarbonate and nitriles catalyzed by Cu(OTf)2
-
The utility of Cu(OTf)2 as the catalyst for the synthesis of a series of N-tert-butyl amides in excellent isolated yields via the reaction of nitriles (alkyl, aryl, benzyl, and furyl nitriles) with di-tert-butyl dicarbonate is described. Cu(OTf)2 is a highly stable and efficient catalyst for the present Ritter reaction under solvent-free conditions at room temperature.
- Chen, Junqing,Feng, Chengliang,Ji, Min,Tang, Yuqi,Yang, Wanfeng
-
p. 602 - 608
(2020/04/27)
-
- Organophotoredox-Mediated Amide Synthesis by Coupling Alcohol and Amine through Aerobic Oxidation of Alcohol
-
The combination of an organic photocatalyst [4CzIPN (1,2,3,5-tetrakis(carbazol-9-yl)-4,6 dicyanobenzene) or 5MeOCzBN (2,3,4,5,6-pentakis(3,6-dimethoxy-9 H-carbazol-9-yl)benzonitrile)], quinuclidine, and tetra-n-butylammonium phosphate (hydrogen-bonding catalyst) was employed for amide bond formations. The hydrogen-bonded OH group activated the adjacent C?H bond of alcohols towards hydrogen atom transfer (HAT) by a radical species. The quinuclidinium radical cation, generated through single-electron oxidation of quinuclidine by the photocatalyst, employed to abstract a hydrogen atom from the α-C?H bond of alcohols selectively due to a polarity effect-produced α-hydroxyalkyl radical, which subsequently converted to the corresponding aldehyde under aerobic conditions. Then the coupling of the aldehyde and an amine formed a hemiaminal intermediate that upon photocatalytic oxidation produced the amide.
- Samanta, Samya,Shah, Sk. Sheriff,Shee, Maniklal,Singh, Amit Kumar,Singh, N. D. Pradeep,Venkatesh, Yarra
-
-
- CoFe2O4?SiO2-NH-βCD-BF3 as a supramolecular nanocomposite: Synthesis, characterization and catalytic activity
-
This manuscript describes synthesis of BF3-functionlized β-cylcodextrine grafted magnetic CoFe2O4 nanaoparticles as a hybrid magnetic nano-composite (CoFe2O4?SiO2-NH-βCD-BF3). The CoFe2O4?SiO2-NH-βCD-BF3 was fabricated by grafting of 6-O-toluenesulfonyl cyclodextrin (6-Ts-βCD) to 3-aminopropyl triethoxysilane coated magnetic CoFe2O4?SiO2 nanoparticles followed by combination with BF3. The CoFe2O4?SiO2-NH-βCD-BF3was characterized by FT-IR, TGA, VSM and SEM techniques. The feasibility of using CoFe2O4?SiO2-NH-βCD-BF3 as a magnetically recoverable catalyst was confirmed in the modified-Ritter reaction. The result showed that this novel nano-composite could serve as an efficient nanoreactor bearing super-acidic sites formed by immobilized BF3 and reuse at least for 6 times without loss in activity.
- Hamadi, Hosein,Zanjani, Zohreh,Yadollahi, Mahtab
-
-
- Rh(III)-Catalyzed Distal C-H Alkenylation of Weakly Coordinating Acetamides Via Desilylation Pathway
-
Rh(III)-Catalyzed distal ortho-C?H alkenylation of arylacetamides have been reported employing acetamide, a weak coordinating group, as a directing group. This challenging C?H alkenylation of arylacetamides has been achieved by using arylalkynyl silanes as a surrogate for terminal alkynes under redox neutral process through desilylation pathway. The control experiments suggest that the in situ generatedRh-species is likely to be Lewis acidic, which is playing a vital role in the desilylation step. (Figure presented.).
- Ramesh, Vinay Bapu,Muniraj, Nachimuthu,Prabhu, Kandikere Ramaiah
-
supporting information
p. 3683 - 3688
(2019/07/12)
-
- Ruthenium-Catalyzed Oxidative Amidation of Alkynes to Amides
-
Complex CpRuCl(PPh3)2 catalyzes reactions of terminal alkynes with 4-picoline N-oxide and primary and secondary amines to afford the corresponding amides. The reactions occur in chlorinated solvent and aqueous medium, showing applications in peptide chemistry. Stoichiometric studies reveal that the true catalysts of the processes are the vinylidene cations [CpRu(=C=CHR)(PPh3)2]+ which are oxidized to the Ru(η2-CO)-ketenes by the N-oxide. Finally, nucleophilic additions of primary and secondary amines to the free ketenes yield the corresponding amides.
- álvarez-Pérez, Andrea,Esteruelas, Miguel A.,Izquierdo, Susana,Varela, Jesús A.,Saá, Carlos
-
supporting information
p. 5346 - 5350
(2019/07/08)
-
- An efficient synthesis of N-tert-butyl amides by the reaction of tert-butyl benzoate with nitriles catalyzed by Zn(ClO4)2·6H2O
-
An efficient, mild and inexpensive synthesis of N-tert-butyl amides from the reaction of nitriles (aryl, benzyl and sec-alkyl nitriles) with tert-butyl benzoate catalyzed by the employment of 2?mol% Zn(ClO4)2·6H2O at 50?°C
- Feng, Cheng-Liang,Yan, Bin,Zhang, Min,Chen, Jun-Qing,Ji, Min
-
p. 535 - 542
(2019/02/12)
-
- Fe(ClO 4) 3 ·h 2 O-Catalyzed Ritter Reaction: A Convenient Synthesis of Amides from Esters and Nitriles
-
An efficient and inexpensive synthesis of N-substituted amides from the Ritter reaction of nitriles with esters catalyzed by Fe(ClO 4) 3 ·H 2 O is described. Fe(ClO 4) 3 ·H 2 O is an economically efficient catalyst for the Ritter reaction under solvent-free conditions. Reactions of a range of esters (benzyl, sec-alkyl, and tert-butyl esters) with nitriles (primary, secondary, tertiary, and aryl nitriles) were performed to provide the corresponding amides in high to excellent yields.
- Feng, Chengliang,Yan, Bin,Yin, Guibo,Chen, Junqing,Ji, Min
-
p. 2257 - 2264
(2018/10/20)
-
- β-Lactam Synthesis through Diodomethane Addition to Amide Dianions
-
We present a novel route for the quick and easy synthesis of a broad range of β-lactams. The synthesis involves a [3+1] cyclization of amide dianions with diiodomethane. In contrast to the seminal work of Hirai et al. from 1979, the reaction proved to be
- Zidan, Alaa,Garrec, Julian,Cordier, Marie,El-Naggar, Abeer M.,Abd El-Sattar, Nour E. A.,Khalil, Ali,Hassan, Mohamed Ali,El Kaim, Laurent
-
supporting information
p. 12179 - 12183
(2017/09/06)
-
- Organic template-free synthesis of zeolite Y nanoparticle assemblies and their application in the catalysis of the Ritter reaction
-
Zeolite Y nanoparticle assemblies (Y-NA) with a mesoporous structure were directly synthesized at 75?°C for 16 h without adding any organic templates. The changes in structure, morphology and textural parameters of the materials obtained after different crystallization times were investigated via powder X-ray diffraction (XRD), infrared spectroscopy (IR), scanning electron microscopy (SEM), transmission electron microscopy (TEM) and N2-sorption. The results show that Y-NA had a micro-mesoporous structure composed of highly crystalline particle assemblies with sizes of 400-900 nm. The H-form Y-NA (HY-NA) is strongly acidic, and exhibits a good catalytic performance in the Ritter reaction, as compared with the H-form microporous zeolite Y and mesoporous zeolite ZSM-5.
- Tang, Ting,Zhang, Lei,Dong, Hai,Fang, Zhongxue,Fu, Wenqian,Yu, Quanyong,Tang, Tiandi
-
p. 7711 - 7717
(2017/02/05)
-
- Efficient Approach to Amide Bond Formation with Nitriles and Peroxides: One-Pot Access to Boronated β-Ketoamides
-
An efficient, mild and practical approach for the synthesis of amides from nitriles and peroxides is reported in the presence of boron trifluoride ethereate. In this protocol, we utilized peroxides as C1 synthons for the amidation reaction. Als
- Gore, Babasaheb Sopan,Senadi, Gopal Chandru,Garkhedkar, Amol Milind,Wang, Jeh-Jeng
-
supporting information
p. 3014 - 3021
(2017/09/08)
-
- Nickel-Catalyzed Reductive Addition of Aryl/Benzyl Halides and Pseudohalides to Carbodiimides for the Synthesis of Amides
-
A Nickel-catalyzed reductive process is described for the direct amidation of benzyl and aryl halides using carbodiimides as the amidating agent. Moreover, aryl and benzyl C–O electrophiles such as triflate, acetate, tosylate, trityl ether, and pivalate were converted into amides using this method. The in-situ-generated Ni0acts as a catalyst for the reaction at room temperature for benzylic substrates, and 70 °C for aryl electrophiles. This new nickel-catalyzed reductive coupling protocol provides a general and operationally simple method for the synthesis of diverse amides using carbodiimides. Amides bearing bulky substituents can be synthesized by this strategy in high yield, which demonstrates its effectiveness in amide synthesis.
- Panahi, Farhad,Jamedi, Fereshteh,Iranpoor, Nasser
-
p. 780 - 788
(2017/01/18)
-
- Sterically Demanding Oxidative Amidation of α-Substituted Malononitriles with Amines Using O2
-
An efficient amidation method between readily available 1,1-dicyanoalkanes and either chiral or nonchiral amines was realized simply with molecular oxygen and a carbonate base. This oxidative protocol can be applied to both sterically and electronically challenging substrates in a highly chemoselective, practical, and rapid manner. The use of cyclopropyl and thioether substrates support the radical formation of α-peroxy malononitrile species, which can cyclize to dioxiranes that can monooxygenate malononitrile α-carbanions to afford activated acyl cyanides capable of reacting with amine nucleophiles.
- Li, Jing,Lear, Martin J.,Hayashi, Yujiro
-
supporting information
p. 9060 - 9064
(2016/07/26)
-
- Microwave assisted, Ca(II)-catalyzed Ritter reaction for the green synthesis of amides
-
An efficient solvent-free synthesis of amides by Ca(II) catalyzed Ritter reaction has been reported under microwave irradiation. This green protocol tolerates the substrate diversity and delivers the high yielding amides with minimal loading of inexpensive and more abundant Ca(II) catalyst.
- Yaragorla, Srinivasarao,Singh, Garima,Lal Saini, Pyare,Reddy, M. Kesava
-
p. 4657 - 4660
(2014/12/10)
-
- Direct synthesis of amides from carboxylic acids and amines using B(OCH2CF3)3
-
B(OCH2CF3)3, prepared from readily available B2O3 and 2,2,2-trifluoroethanol, is as an effective reagent for the direct amidation of a variety of carboxylic acids with a broad range of amines. In most cases, the amide products can be purified by a simple filtration procedure using commercially available resins, with no need for aqueous workup or chromatography. The amidation of N-protected amino acids with both primary and secondary amines proceeds effectively, with very low levels of racemization. B(OCH2CF3)3 can also be used for the formylation of a range of amines in good to excellent yield, via transamidation of dimethylformamide.
- Lanigan, Rachel M.,Starkov, Pavel,Sheppard, Tom D.
-
p. 4512 - 4523
(2013/06/05)
-
- Amide formation using in situ activation of carboxylic acids with [Et 2NSF2]BF4
-
The formation of amides through the in situ activation of carboxylic acids with [Et2NSF2]BF4 is presented. A wide range of carboxylic acids and amines were used to produce the corresponding amides in up to 99 % yield. The reaction of hindered amines was also possible in the presence of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) under slightly modified conditions. An enantiopure carboxylic acid and amine were both shown to react without racemization. Copyright
- Mahe, Olivier,Desroches, Justine,Paquin, Jean-Francois
-
p. 4325 - 4331
(2013/07/26)
-
- KAl(SO4)2.12H2O as an eco-friendly and reusable catalyst for the synthesis of amides by the Ritter reaction
-
KAl(SO4)2.12H2O (Alum) is an eco-friendly, inexpensive, readily available and reusable and was applied as catalyst to the synthesis of N-alkyl amides from nitriles and alcohols by the Ritter reaction. This solvent-free procedure is very simple with excellent yields and easy work-up.
- Sadeghi, Bahareh,Farahzadi, Ebrahim,Hassanabadi, Alireza
-
p. 539 - 540
(2012/10/30)
-
- Ritter reaction in subcritical water: An efficient and green method for amides synthesis
-
Ritter reaction was carried out efficiently in subcritical water with catalytic amount of trifluoromethanesulfonic acid. The amides were formed in good to excellent yields from secondary alcohols and tert-butanol with various nitriles.
- Jiang, Shengqian,Wang, Zhouyu,Jiang, Zhenju,Li, Jianhui,Zhou, Shulin,Pu, Long
-
experimental part
p. 24 - 28
(2012/08/08)
-
- SO42-/CexZr1-xO2-catalyzed synthesis of N-tert-butylamides from various nitriles under solvent-free conditions
-
The synthesis of N-tert-butylamides using SO4 2-/CexZr1-x O2 catalysts under solvent-free conditions is reported. The methodology has several advantages such as reusability of the catalyst, solvent-free conditions, easy workup, and comparable yield of N-tert-butylamides. A variety of aliphatic, aromatic, and acid-sensitive substrates give high to moderate yields of the corresponding N-tert-butylamides. Surface acidities of the catalysts were correlated with the results obtained. To the best of our knowledge, this is the first report of a modified Ritter reaction on SO42-/CexZr1-x O2 using tert-butyl acetate as carbocationic source.
- Kahandal, Sandeep S.,Kale, Sandip R.,Disale, Shamrao T.,Jayaram, Radha V.
-
experimental part
p. 738 - 740
(2012/09/22)
-
- Sulfated tungstate: An efficient catalyst for the Ritter reaction
-
The use of sulfated tungstate as an efficient and reusable catalyst for the preparation of amides from alcohols and nitriles via the Ritter reaction pathway is discussed. The reaction proceeds under solvent free conditions. The Royal Society of Chemistry.
- Katkar, Kamlesh V.,Chaudhari, Pramod S.,Akamanchi, Krishnacharya G.
-
supporting information; experimental part
p. 835 - 838
(2011/05/15)
-
- Palladium-catalyzed amidation of N-tosylhydrazones with isocyanides
-
Aminocarbonylation of N-tosylhydrazones: The direct formation of ketenimines from carbenes and isocyanides is limited to the reaction of Fischer carbene complexes or some specially stabilized carbenes with isocyanides. A Pd-catalyzed amidation of N-tosylhydrazones with isocyanides via a ketenimine intermediate in the presence of water is described. The method offers a general way to synthesize amides from carbonyl compounds through one-carbon extension (see scheme). Copyright
- Zhou, Fengtao,Ding, Ke,Cai, Qian
-
experimental part
p. 12268 - 12271
(2011/11/29)
-
- One-pot esterification and Ritter reaction: Chemo- and regioselectivity from tert-butyl methyl ether
-
tert-Butyl methyl ether (TBME) has been effectively used as a reagent for esterification of carboxylic acids. By varying amounts of sulfuric acid, a remarkable regioselectivity in esterification has been demonstrated. Additionally, under the present reaction conditions, one-pot esterification and Ritter reaction are achieved in almost quantitative yield.
- Dawar, Pankaj,Bhagavan Raju,Ramakrishna, Ramesha A.
-
scheme or table
p. 4262 - 4265
(2011/08/21)
-
- Synthesis of amides via palladium-catalyzed amidation of aryl halides
-
A new and efficient method for the synthesis of amides via palladium-catalyzed C-C coupling of aryl halides with isocyanides is reported, by which a series of amides were formed from readily available starting materials under mild conditions. This transformation could extend its use to the synthesis of natural products and significant pharmaceuticals.(Figure Presented)
- Jiang, Huanfeng,Liu, Bifu,Li, Yibiao,Wang, Azhong,Huang, Huawen
-
supporting information; experimental part
p. 1028 - 1031
(2011/04/27)
-
- Organocatalytic synthesis of amides from nitriles via the Ritter reaction
-
A simple, inexpensive, environmentally friendly, and efficient route for the synthesis of a wide variety of amides in high yields via the Ritter reaction of alcohols with nitriles has been demonstrated. Pentafluorophenyl ammonium triflate (PFPAT) is used as an organocatalyst and is air-stable, cost-effective, easy to handle, and easily removed from the reaction mixtures.
- Khaksar, Samad,Fattahi, Eskandar,Fattahi, Esmail
-
experimental part
p. 5943 - 5946
(2011/11/28)
-
- Iodine-catalyzed one-pot synthesis of amides from nitriles via Ritter reaction
-
Ritter reactions of alcohols and tert-butyl acetate with various nitriles were performed using iodine as a mild and effective catalyst under heating conditions to afford the corresponding amides in good to excellent yields.
- Theerthagiri, Palani,Lalitha, Appaswami,Arunachalam, Pirama Nayagam
-
supporting information; experimental part
p. 2813 - 2819
(2010/07/04)
-
- Umpolung reactivity in amide and peptide synthesis
-
The amide bond is one of natureg€s most common functional and structural elements, as the backbones of all natural peptides and proteins are composed of amide bonds. Amides are also present in many therapeutic small molecules. The construction of amide bonds using available methods relies principally on dehydrative approaches, although oxidative and radical-based methods are representative alternatives. In nearly every example, carbon and nitrogen bear electrophilic and nucleophilic character, respectively, during the carbong€"nitrogen bond-forming step. Here we show that activation of amines and nitroalkanes with an electrophilic iodine source can lead directly to amide products. Preliminary observations support a mechanism in which the polarities of the two reactants are reversed (German, umpolung) during carbong€"nitrogen bond formation relative to traditional approaches. The use of nitroalkanes as acyl anion equivalents provides a conceptually innovative approach to amide and peptide synthesis, and one that might ultimately provide for efficient peptide synthesis that is fully reliant on enantioselective methods.
- Shen, Bo,Makley, Dawn M.,Johnston, Jeffrey N.
-
scheme or table
p. 1027 - 1032
(2011/08/06)
-
- One-pot amide synthesis from allyl or benzyl halides and amines by Pd-catalysed carbonylation
-
Amides can be prepared from allyl or benzyl halides and primary or secondary amines, using Pd(0) catalyst under CO pressure, in a one-pot synthesis. The reaction proceeds through the acyl palladium halide formation which undergoes an acylic nucleophilic substitution from the amine.
- Troisi, Luigino,Granito, Catia,Rosato, Francesca,Videtta, Valeria
-
experimental part
p. 371 - 373
(2010/03/24)
-
- An efficient and scalable ritter reaction for the synthesis of tert-butyl amides
-
A scalable procedure for the conversion of nitriles to N-tert-butyl amides via the Ritter reaction was optimized employing tert-butyl acetate and acetic acid. The reaction has a broad scope for aromatic, alkyl, and α,β-unsaturated nitriles.
- Baum, Jean C.,Milne, Jacqueline E.,Murry, Jerry A.,Thiel, Oliver R.
-
supporting information; experimental part
p. 2207 - 2209
(2009/07/01)
-
- FeCl3-catalyzed Ritter reaction. Synthesis of amides
-
A safe and inexpensive synthesis of amides, from benzylic alcohols and nitriles and from t-butyl acetate and nitriles, using a Ritter reaction catalyzed by FeCl3·6H2O is described.
- Anxionnat, Bruno,Guérinot, Amandine,Reymond, Sébastien,Cossy, Janine
-
experimental part
p. 3470 - 3473
(2009/09/28)
-
- Formation of acrylanilides, acrylamides, and amides directly from carboxylic acids using thionyl chloride in dimethylacetamide in the absence of bases
-
A general one-pot procedure is described that rapidly converts acrylic acid to anilides upon sequential treatment of the acid in dimethylacetamide (DMAC) with thionyl chloride and stoichiometric amounts of anilines in 88-98% yields, with DMAC offering rate and stability advantages over the use of DMF. The use of DMAC was extended to other organic acids in forming anilides. Benzylamine amides can also be formed using stoichiometric amounts of benzylamine and brought to completion by warming in the absence of additional base. In addition, it was shown that tert-butylamides can be easily formed with the addition of excess tert-butylamine at 20 °C.
- Cvetovich, Raymond J.,DiMichele, Lisa
-
p. 944 - 946
(2012/12/23)
-
- New observations on peptide bond formation using CDMT
-
The optimized formation of the peptide bond by means of 2-chloro-4,6-dimethoxy-1,3,5-triazine (CDMT) has been found to occur rapidly and essentially quantitatively in a one-pot, one-step procedure. This new method is effective for the coupling of a variety of reactive partners, including chiral amino acids (e.g. N-acetyl-L-leucine) without significant loss of configuration. Significant racemization was observed when the typical literature conditions were used, due to the formation of an azlactone intermediate which is configurationally unstable under the reaction conditions. A simpler, precipitative workup procedure is also disclosed in this report.
- Garrett, Christine E.,Jiang, Xinglong,Prasad, Kapa,Repi?, Oljan
-
p. 4161 - 4165
(2007/10/03)
-
- Facile conversion of alcohols into N-substituted amides by magnesium hydrogensulfate under heterogeneous conditions
-
Different classes of alcohols react efficiently with nitriles in the presence of magnesium hydrogensulfate, Mg(HSO4)2, to produce amides in high yields.
- Salehi,Khodaei,Zolfigol,Keyvan
-
p. 1947 - 1951
(2007/10/03)
-
- Fe3+-montmorillonite K10: An efficient catalyst for selective amidation of alcohols with nitriles under non-aqueous condition
-
An efficient method for preparation of secondary amides by reaction of alcohols with nitriles is described using a catalytic amount of Fe3+- montmorillonite K10.
- Lakouraj,Movassagh,Fasihi
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p. 821 - 827
(2007/10/03)
-
- Adamantylation and adamantylalkylation of amides, nitriles, and ureas in trifluoroacetic acid
-
A new preparative procedure was developed for N-adamantylation of carboxylic acids amides and ureas, and C5-adamantylation of barbituric acid in trifluoroacetic acid medium with tertiary adamantanols and 1-adamantylalkanols. The reaction of 2-adamantanols and secondary 1-adamantylalkanols with nitriles was for the first time used in the preparation of W-(2-adamantyl)-and N-(1-adamantylalkyl)amides.
- Shokova,Musulu, Tasula,Luzikov,Kovalev
-
p. 844 - 856
(2007/10/03)
-
- Adamantylation and adamantylalkylation of amides, nitriles and ureas in trifluoroacetic acid
-
A new preparative method for N-adamantylation of carboxylic acid amides, ureas and for C5-adamantylation of barbituric acid in trifluoroacetic acid (TFA) is proposed. Tertiary 1-adamantanols and 1-(1-adamantyl)alkanols were used as adamantylating agents. The reaction of 1-(1-adamantyl)alkanols with nitriles in TFA solution was employed for the first time for the preparation of N-[1-(1-adamantyl)alkyl]amides.
- Shokova, Elvira,Mousoulou, Tasoulla,Luzikov, Yurij,Kovalev, Vladimir
-
p. 1034 - 1040
(2007/10/03)
-
- Direct conversion of esters to secondary amides using Tin(II) reagents
-
We have developed tow new procedures for the direct conversion of esters to secondary amides. In our first procedure, secondary amides can be prepared in 83-98% yield starting from glycol esters. Addition of Sn[N(TMS)2]2 and a primary amine to the glycol ester generates an intermediate tin(II) akoxy amide, which delivers the amino group intramolecularly to give the amide. A second general procedure for the preparation of secondary amides starts with methyl esters. Treatment of methyl esters with a tin reagent derived from Sn[N(TMS)2]2, Me2NCH2CH2OH, and a primary amine yields secondary amides in 87-98% yield.
- Wang,Restituyo,Roskamp
-
p. 7217 - 7220
(2007/10/02)
-
- Anodic Oxidation of Di-tert-butyl Disulfide: a Facile Method for the Preparation of N-tert-Butylamides
-
The electrochemical oxidation of di-tert-butyl disulfide is shown to correspond to a one electron process; at 1.3 V, one carbon-sulfur bond is cleaved yielding two intermediate species; the tert-butyl cation and the radical t-BuS-S; a Ritter reaction occurs with the cation when the solvent is a nitrile and the cation dimerizes into a tetrasulfide; at a more positive potential (1.9 V) the two carbon-sulfur bonds are cleaved giving t-Bu cation and sulfur.
- Elothmani, Driss,Do, Quang Tho,Simonet, Jacques,Guillanton, Georges Le
-
p. 715 - 717
(2007/10/02)
-
- 3-ACYL-2-(N-CYANOIMINO)THIAZOLIDINES AS AN ACYLATING AGENT. PREPARATION OF AMIDES, ESTERS, AND THIOESTERS
-
3-Acyl-2-(N-cyanoimino)thiazolidines proved to be powerful acylating agents.They reacted easily with amines, alcohols and thiols to give the corresponding amides, esters and thioesters in good yields.
- Iwata, Chuzo,Watanabe, Mayumi,Okamoto, Shigeha,Fujimoto, Michitaro,Sakae, Masatoshi,et al.
-
p. 323 - 326
(2007/10/02)
-
- Reactions of 1-tert-Butyl-3-phenylaziridinone and α-Bromo-N-tert-butylphenylacetamide with Benzyl-Grignard Reagents
-
1-tert-Butyl-3-phenylaziridinone (1) reacts with benzyl halide Grignard reagents (Br and Cl) to give N-tert-butyl-2,3-diphenylpropanamide (4), N-tert-butyl-2-phenylacetamide (3), N-tert-butyl-2-o-tolyl-2-phenylacetamide (5), 1-(tert-butylamino)-1,3-diphenylpropan-2-one (7), N-benzyl-N-tert-butyl-2-phenylacetamide (6), and N-tert-butyl-2-halo-2-phenylacetamide (2, X = Br, Cl).The choice of solvent appears to determine the relative amounts of products 4 and 5.The bromo amide 2 reacts with the Grignard reagent to give 3, 4, 5, 6, and 7 and may be involved to some extentin the reaction of 1 with benzyl-Grignard reagents.The formation of 5 represents anew type of "abnormal" product from a reaction of the benzyl-Grignard reagent; however, this product appears to fit well into the mechanistic pattern established for prior examples.
- Baumgarten, Henry E.,Chiang, Nein-Chu Robert,Elia, Victor J.,Beum, Paul V.
-
p. 5507 - 5512
(2007/10/02)
-