Synthesis of structurally constrained 4-quinazolinone derivatives with a tetrahedral C-2 atom present in three rings

被引：13

作者：

Iminov, Rustam T. ^{[2
]}

Tverdokhlebov, Anton V. ^{[1
]}

Tolmachev, Andrey A. ^{[1
,2
]}

Volovenko, Yulian M. ^{[2
]}

Shishkina, Svetlana V. ^{[3
]}

Shishkin, Oleg V. ^{[3
]}

机构：

[1] Enamine Ltd, UA-01103 Kiev, Ukraine

[2] Kiev Natl Taras Shevchenko Univ, UA-01033 Kiev, Ukraine

[3] NAS Ukraine, STC Inst Single Crystals, UA-61001 Kharkov, Ukraine

来源：

TETRAHEDRON | 2009年 / 65卷 / 41期

关键词：

Aminals; 2-Aminobenzamides; Condensed heterocycles; 4-Oxoacids; Quinazolines; AROMATISCHEN ERYTHRINA-ALKALOIDE; N-NITRENES; SATURATED HETEROCYCLES; SYNTHETISCHE ARBEITEN; TRICYCLIC DERIVATIVES; QUINAZOLINE; QUINOLINE; OXIDATION; REIHE; ACIDS;

D O I：

10.1016/j.tet.2009.07.059

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The reaction of 2-aminobenzamides with 2-oxocyclopentane-, 2-oxocyclohexane-, and 2-oxocycloheptaneacetic acids esters was found to give 7a,8,9,10-tetrahydrocyclopenta[2,3]pyrrolo[1,2-a]quinazoline-6,12(7H,11H)-diones, 7,7a,8,9,10,11-hexahydro-6H-indolo[1,7a-a]quinazoline-6,13(12H)-diones, and 7a,8,9,10.11,12-hexahydrocyclohepta[2,3]pyrrolol[1,2-a]quinazoline-6,14(7H,13H)-diones, respectively. The relative configuration with the cis-fused butyrolactam and cycloalkane rings was assigned to the prepared compounds on the basis of an X-ray crystallographic study. (C) 2009 Elsevier Ltd. All rights reserved.

引用

页码：8582 / 8586

页数：5

共 59 条

[1] Facile and highly stereoselective synthesis of the tetracyclic erythrinane core [J].