Synthesis of 5-thioxo-6H-imidazo[1,2-c]quinazolines and related compounds based on cyclocondensations of 2-isothiocyanatobenzonitrile (ITCB) with α-aminoketones

被引：8

作者：

Bodtke, Anja ^{[2
]}

Pfeiffer, Wolf-Diethard ^{[3
]}

Goerls, Helmar ^{[4
]}

Dollinger, Horst

Langer, Peter ^{[1
,5
]}

机构：

[1] Univ Rostock, Inst Chem, D-18059 Rostock, Germany

[2] Ernst Moritz Arndt Univ Greifswald, Inst Biochem, D-17487 Greifswald, Germany

[3] Univ Jena, Inst Anorgan & Analyt Chem, D-07740 Jena, Germany

[4] Boehringer Ingelheim Pharm GmbH & Co KG, D-88397 Biberach, Germany

[5] Univ Rostock, Leibniz Inst Katalyse e V, D-18059 Rostock, Germany

来源：

TETRAHEDRON | 2007年 / 63卷 / 46期

关键词：

cyclizations; N-heterocycles; isocyanates; isothiocyanates; sequential reactions;

D O I：

10.1016/j.tet.2007.08.090

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Pharmacologically relevant 5-thioxo-6H-imidazo[1,2-c]quinazolines and 5-oxo-6H-imidazo[1,2-c]quinazolines were prepared by sequential reactions of alpha-aminoketones with 2-isothiocyanatobenzonitrile (ITCB) and 2-isocyanatobenzonitrile (ICB), respectively. The functionalization of the thioxo moiety allowed the synthesis of 5-amino-6H-imidazo[1,2-c]quinazolines and of 1,2,4-triazolo[4,3-alpha]-imidazo[1,2-c]quinazolines. (C) 2007 Elsevier Ltd. All rights reserved.

引用

页码：11287 / 11298

页数：12

共 6 条

[1] Synthesis of 2-oxo-2,3,5,6-tetrahydro-5-thioxoimidazo[1,2-c]quinazolines by one-pot cyclization of α-aminocarboxylic esters with 2-(isothiocyanato)benzonitrile (ITCB)
Bodtke, Anja
Reinke, Helmut
Michalik, Dirk
Langer, Peter
TETRAHEDRON, 2006, 62 (33) : 7653 - 7660
[2] Synthesis of Imidazo[1,2-c]quinazolin-5(6H)-ones and Benzimidazo[1,2-c]quinazolin-6(5H)-ones with the Aid of Low-Valent Titanium Reagent
Zhao, Xuan
Shi, Da-Qing
JOURNAL OF HETEROCYCLIC CHEMISTRY, 2010, 47 (03) : 524 - 527
[3] Domino cyclization of 2-isothiocyanatobenzonitrile with carboxylic hydrazides -: One-pot synthesis of 1,2,4-triazolo[1,5-c]quinazoline-5(6H)-thiones
Blank, J
Kandt, M
Pfeiffer, WD
Hetzheim, A
Langer, P
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2003, 2003 (01) : 182 - 189
[4] Synthesis of 5-Thioxo-hexahydrobenzo[b]thiopheno[2,3-d]-1,2,4-triazolo[1,5-c]pyrimidines and Related Compounds Based on Cyclocondensations of 2-Isothiocyanato-3-cyano-4,5,6,7-tetrahydrobenzo[b]thiophene
Pfeiffer, Wolf-Diethard
Dollinger, Horst
Langer, Peter
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2009, 184 (03) : 626 - 637
[5] Regioselective anionic [3+2] cyclizations of isoxazole, pyrazole and 1,2,4-triazole dinucleophiles -: Efficient synthesis of 2,4-dihydroimidazo-[4,5-b]quinoxalines, 3H-imidazo[1,2-b]pyrazoles and 5H-imidazo[2,1-c][1,2,4]triazoles
Langer, P
Wuckelt, J
Döring, M
Schreiner, PR
Görls, H
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2001, 2001 (12) : 2257 - 2263
[6] Synthesis of 3-Acylpyrroles, 3-(Alkoxycarbonyl)pyrroles, 1,5,6,7-Tetrahydro-4H-indol-4-ones and 3-Benzoylpyridines Based on Staudinger-Aza-Wittig Reactions of 1,3-Dicarbonyl Compounds with 2-and 3-Azido-1,1-dialkoxyalkanes
Bellur, Esen
Yawer, Mirza A.
Hussain, Ibrar
Riahi, Abdolmajid
Fatunsin, Olumide
Fischer, Christine
Langer, Peter
SYNTHESIS-STUTTGART, 2009, (02): : 227 - 242

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