13313-25-2Relevant academic research and scientific papers
Facile Preparation of N-Vinylisobutyramide and N-Vinyl-2-pyrrolidinone
Tu, Siyu,Zhang, Chunming
, p. 2045 - 2049 (2015)
A facile synthesis of N-vinylakylamides from commercially available N-vinylformamide and corresponding acyl chlorides was developed and exemplified by the preparation of N-vinylisobutyramide (NVIBA) and N-vinyl-2-pyrrolidinone (NVP) in high yields (80-89%). Both NVIBA and NVP are valuable monomers for water-soluble polymers with an array of applications in personal care, pharmaceutical, agricultural, and industrial products.
Br?nsted Acid-Promoted Diastereoselective [4+1] Cyclization Reaction of Enamides and Sulfoxonium Ylides
Luo, Nan,Zhan, Zhenzhen,Ban, Zihui,Lu, Guoqiang,He, Jianping,Hu, Fangpeng,Huang, Guosheng
supporting information, p. 3126 - 3130 (2020/07/06)
A metal-free synthesis of trisubstituted trans-oxazolines using enamides and sulfoxonium ylides was developed in this study. A [4+1] cyclization reaction was realized by the formation of C?C and C?O bonds under mild conditions, wherein the reaction was catalyzed by HClO4. This strategy produced trans-oxazolines in good yields with considerable diastereoselective control and is sufficient for large-scale synthesis. (Figure presented.).
Catalytic Strategy for Regioselective Arylethylamine Synthesis
Boyington, Allyson J.,Seath, Ciaran P.,Zearfoss, Avery M.,Xu, Zihao,Jui, Nathan T.
supporting information, p. 4147 - 4153 (2019/03/07)
A mild, modular, and practical catalytic system for the synthesis of the highly privileged phenethylamine pharmacophore is reported. Using a unique combination of organic catalysts to promote the transfer of electrons and hydrogen atoms, this system performs direct hydroarylation of vinyl amine derivatives with a wide range of aryl halides (including aryl chlorides). This general and highly chemoselective protocol delivers a broad range of arylethylamine products with complete regiocontrol. The utility of this process is highlighted by its scalability and the modular synthesis of an array of bioactive small molecules.
Rh(III)-Catalyzed [4 + 2] Self-Annulation of N-Vinylarylamides
Sun, Rui,Yang, Xiao,Chen, Xue,Zhang, Chunchun,Zhao, Xiaoyu,Wang, Xin,Zheng, Xueli,Yuan, Maolin,Fu, Haiyan,Li, Ruixiang,Chen, Hua
supporting information, p. 6755 - 6759 (2018/11/21)
An efficient rhodium(III)-catalyzed self-annulation of N-vinylarylamide has been developed. This reaction features a simple system and good reactivity with complete regioselectivity. The protocol provides easy access to an aminal incorporated dihydroisoqu
A convenient synthesis of N-vinyl enamides via the lithiation and ring-opening reaction of 2-phenyl-2-oxazolines
Xu, Yi,Liu, Xiao-Yu,Wang, Zi-Qi,Tang, Liang-Fu
, p. 1788 - 1791 (2017/04/13)
A simple and efficient synthesis of N-vinyl enamides via the lithiation and ring-opening reaction of 2-phenyl-2-oxazolines with lithium diisopropylamide at room temperature has been developed. This method is especially suitable for the synthesis of multif
Vinylation of pyridylcarboxamides with vinyltrimethoxysilane
Arsenyan,Petrenko,Belyakov
, p. 1527 - 1532 (2018/01/27)
A convenient method has been developed for the direct N-vinylation of pyridylcarboxamides with vinyltrimethoxysilane in the presence of copper(II) acetate and tetrabutylammonium fluoride. The yield of N-vinylamides depends on the nature of the starting amide and the solvent. The molecular structure of the products was confirmed by X-ray structural analysis.
N-(1-Acylaminoalkyl)amidinium salts derived from DBU or related bases as reactive intermediates in α-amidoalkylation reactions
Pazdzierniok-Holewa, Agnieszka,Adamek, Jakub,Zielinska, Katarzyna,Piernikarczyk, Katarzyna,Mazurkiewicz, Roman
, p. 314 - 329 (2013/09/24)
1-(N -Acylamino)alkyltriphenylphosphonium salts 4, when treated with DBU, DBN or TBD in CD3 CN or MeCN, were transformed immediately into the corresponding 1-(N- acylamino)alkylamidinium or guanidinium salts 5. Salts 5 with a proton at the α-position underwent slow transformation to the corresponding enamides 6. 1-(N- Acylamino)alkyltriphenylphosphonium salts 4, amidinium or guanidinium salts 5, as well as enamides 6 reacted readily with β-dicarbonyl compounds in the presence of corresponding base under microwave irradiation at 60 °C to give the expected product of α-amidoalkylation of the enolate anion. The role of 1-(N-acylamino) alkylamidinium or guanidinium salts 5 as reactive intermediates in α-amidoalkylation with 1-(N-acylamino)alkyltriphenylphosphonium salts is discussed. ARKAT-USA, Inc.
Room-temperature palladium(II)-catalyzed N-vinylation of sulfonamides and acylamides with vinyl acetate as vinyl source
Xu, Jun,Fu, Yao,Xiao, Bin,Gong, Tianjun,Guo, Qingxiang
experimental part, p. 5476 - 5479 (2010/10/20)
Room-temperature N-vinylation of various substituted sulfonamides and acylamides with vinyl acetate was achieved for the first time with a palladium/carbene catalyst system. This reaction provides a useful method for synthesis of enamides under mild conditions.
Copper-catalyzed cross-coupling of amides and potassium alkenyltrifluoroborate salts: A general approach to the synthesis of enamides
Boishan, Yuri,Batey, Robert A.
experimental part, p. 5283 - 5294 (2010/08/07)
Potassium alkenyltrifluoroborate salts undergo coupling with amides to give enamides using a catalytic amount of Cu(OAc)2 under mild oxidative conditions. The air and water stable alkenyltrifluoroborate salts offer a practical alternative to the use of alkenyl halides and alkenylboronic acids as cross-coupling partners. A range of amides participate in the cross-coupling, including heterocyclic amides, imides, carbamates, benzamides, and acetamides. Optimization studies established two sets of conditions, best suited to either high PKa or low PKa amide substrates. Lower PK amide substrates worked best using a dichloromethane solvent system in the presence of 4 ? molecular sieves, 10 mol % Cu(OAc)2, and 20 mol % N-methylimidazole. Higher PKa amide substrates worked best using a ligandless protocol using a 1:1 dichloromethane/DMSO solvent system in the presence of 4 ? molecular sieves and 10 mol % Cu(OAc)2. The cross-coupling reactions occur stereospecifically with retention of alkene configuration from the alkenyltrifluoroborate salt. The mild reaction conditions employed are tolerant of various functionalities, including nitro, acetals, alkyl and aryl halides, and α,β-unsaturated carbonyls. Finally, the importance of copper sources and the presence of minor impurities were investigated.
1-(N-Acylamino)alkyltriphenylphosphonium salts as synthetic equivalents of N-acylimines and new effective α-amidoalkylating agents
Mazurkiewicz, Roman,Pa?dzierniok-Holewa, Agnieszka,Orlińska, Beata,Stecko, Sebastian
body text, p. 4606 - 4609 (2009/10/26)
1-(N-Acylaminoalkyl)triphenylphosphonium salts 2a-f on reaction with DBU in MeCN are transformed into 1-(N-acylaminoalkyl)amidinium salts 3a-f. Amidinium salts 3d-f with a proton at the β-position undergo slow tautomerization into the corresponding enamid
