Synthesis of novel 2,3-substituted quinazolin-4-ones by condensation of alkyl or aromatic diamines with 5-(N-arylimino)-4-chloro-5H-1,2,3-dithiazoles

被引：26
|
作者：
Pereira, Maria de Fatima [1 ]
Thiery, Valerie [1 ]
Besson, Thierry [1 ]
机构：
[1] Univ La Rochelle, Lab Biotechnol & Chim Bioorgan, FRE CNRS 2766, UFR Sci Fondamentales & Sci Ingn, F-17042 La Rochelle 1, France
来源：
TETRAHEDRON | 2007年 / 63卷 / 04期
关键词：
4,5-dichloro-1,2,3-dithiazolium chloride (Appel's salt); quinazolin-4-ones; alkanediamines; imino-1,2,3-dithiazoles;
D O I：
10.1016/j.tet.2006.11.028
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The work described in this paper is a further example of the utility of Appel's salt in the conception of novel heterocyclic rings. We confirmed that primary alkyldiamines may react easily with the methyl N-(4-chloro-5H-1,2,3-dithiazol-5-ylidene)-anthranilates to afford quinazolines, which are very interesting starting materials for the access to novel 2,3-condensed quinazolin-4-ones. On the other side, aromatic amines allow the synthesis of polycyclic molecules, which are structurally close to the model natural products (e.g., rutaecarpine, luotonine, tryptanthrine and vasicinone). (c) 2006 Elsevier Ltd. All rights reserved.
引用
收藏
页码：847 / 854
页数：8
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