Synthesis of N1,N3-disubstituted formamidrazones via the TMSCl-promoted reaction of isocyanides with thiosemicarbazones

被引：2

作者：

Sarnpitak, Pakornwit ^{[1
]}

Tsirulnikov, Sergey ^{[2
]}

Krasavin, Mikhail ^{[1
]}

机构：

[1] Griffith Univ, Eskitis Inst Cell & Mol Therapies, Nathan, Qld 4111, Australia

[2] Yaroslavl State Pedag Univ, Sci & Educ Ctr Innovat Res, Yaroslavl 150000, Russia

来源：

TETRAHEDRON LETTERS | 2012年 / 53卷 / 48期

关键词：

Isocyanide-based multicomponent reactions; Isocyanide insertion; Lewis acid catalysis; Chlorotrimethylsilane; Formamidrazones; MULTICOMPONENT REACTIONS; CARBONYL;

D O I：

10.1016/j.tetlet.2012.09.085

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A hitherto undescribed TMSCl-promoted reaction of thiosemicarbazones was found to give rare N-1,N-3-disubstituted formamidrazones in fair to excellent yields. The scope of this new reaction was investigated and a plausible mechanism proposed. (C) 2012 Elsevier Ltd. All rights reserved.

引用

页码：6540 / 6543

页数：4

共 38 条

[21] The Reaction of N-Isocyaniminotriphenylphosphorane With Biacetyl in the Presence of (E)-Cinnamic Acids: Synthesis of Fully Substituted 1,3,4-Oxadiazole Derivatives via Intramolecular AZA-Wittig Reactions of in Situ Generated Iminophosphoranes
Ramazani, Ali
Abdian, Behnaz
Nasrabadi, Fatemeh Zeinali
Rouhani, Morteza
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2013, 188 (05) : 642 - 648
[22] Synthesis of C3-Cyanomethylated Imidazo[1,2-a]pyridines via Ultrasound-Promoted Three-Component Reaction under Catalyst-and Oxidant-Free Conditions
Zhang, Jie
Zhang, Yufeng
Zhang, Jian
Wu, Qingguo
Yang, Haifeng
SYNLETT, 2022, 33 (03) : 264 - 268
[23] Four-Component Synthesis of 2-(N,N-Dialkylamino)-2,4,6-Cycloheptatrien-1-One Derivatives from Tropolone, an Isocyanide, a Primary Amine and an Aldehyde via Ugi-Smiles Coupling Reaction
Massoudi, Abdolhossain
Amini, Issa
Ramazani, Ali
Nasrabadi, Fatemeh Zeinali
Ahmadi, Yavar
BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2012, 33 (01) : 39 - 42
[24] Synthesis of 2-Aryl-5-oxo-4-[2-(phenylmethylidene)hydrazino]-2,5-dihydro-1H-pyrrole-3-carboxylates by the Reaction between Hydrazones, Acetylenedicarboxylates, and 1-Aryl-N,N′-bis(arylmethylidene)methanediamines
Alizadeh, Abdolali
Saberi, Vahid
Mokhtari, Javad
HELVETICA CHIMICA ACTA, 2013, 96 (10) : 1991 - 1996
[25] N-ISOCYANIMINO-TRIPHENYLPHOSPHORANE (PH3PNNC) AS AN EFFICIENT REAGENT FOR THE PREPARATION OF FULLY SUBSTITUTED 1,3,4-OXADIAZOLES VIA INTRAMOLECULAR AZA-WITTIG REACTION IN WATER
Jafari, Ali
Ramazani, Ali
Asiabi, Pegah Azimzadeh
Sadri, Fariba
Joo, Sang Woo
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2015, 190 (12) : 2246 - 2254
[26] Synthesis of N-Alkyl-2-aryl-5H-imidazo[1,2-b]pyrazol-3-amines by a Three-Component Condensation Reaction
Rahmati, Abbas
Kouzehrash, Meysam Alizadeh
SYNTHESIS-STUTTGART, 2011, (18): : 2913 - 2920
[27] An Efficient Synthesis of N-Substituted-3-aryl-3-(2-hydroxy-4,4-dimethyl-6-oxocyclohex-1-enyl)propanamides by Four-component Reaction in Aqueous Medium
Dou Guolan
Zhong Xiaoxing
Wang Deming
Shi Daqing
CHINESE JOURNAL OF CHEMISTRY, 2011, 29 (11) : 2368 - 2372
[28] One-Pot Two-Step Four-Component Synthesis of 1′-N-Methylspiro[2′,11′′]indeno[1,2-b]quinoxalinespiro[3′,2]-6-arylmethylene-cyclohexanone-4′-arylpyrrolidines via [3+2] Cycloaddition Reaction
Tao, H.
RUSSIAN JOURNAL OF GENERAL CHEMISTRY, 2023, 93 (04) : 981 - 986
[29] Synthesis of novel N-functionalized 4-aryl-tetrahydrobiquinoline-2,5-(1H,3H)-diones via one-pot three-component reaction: a joint experimental and computational study
Zadsirjan, Vahideh
Mandizadeh, Sayyed Jalil
Heravi, Majid M.
Heydari, Masumeh
CANADIAN JOURNAL OF CHEMISTRY, 2018, 96 (12) : 1071 - 1078
[30] DEAD-Mediated Oxidative Ugi/Aza-Wittig Reaction for the Synthesis of 5-(1,2,3,4-Tetrahydroisoquinolin-1-yl)-1,3,4-oxadiazoles Starting from (N-Isocyanimine)triphenylphosphorane
Sun, Mei
Zhao, Long
Yu, Yan-Ling
Ding, Ming-Wu
SYNTHESIS-STUTTGART, 2021, 53 (07): : 1365 - 1371

← 1 2 3 4 →