4-Chloro-2-Fluoro-5-Nitrobenzoic Acid as a Possible Building Block for Solid-phase Synthesis of Various Heterocyclic Scaffolds
详细信息 查看全文
- 作者：So艌a K艡upkov谩 ; Petr Funk ; Miroslav Soural ; Jan Hlav谩膷
- 刊名：ACS Combinatorial Science
- 出版年：2013
- 出版时间：January 14, 2013
- 年：2013
- 卷：15
- 期：1
- 页码：20-28
- 全文大小：461K
- 年卷期：v.15,no.1(January 14, 2013)
- ISSN：2156-8944
文摘
4-Chloro-2-fluoro-5-nitrobenzoic acid is a commercially available multireactive building block that can serve as a starting material in heterocyclic oriented synthesis (HOS) leading to various condensed nitrogenous cycles. This work describes its ability for the preparation of substituted nitrogenous heterocycles having 5鈥?-membered cycles via polymer-supported o-phenylendiamines. Immobilization of this compound on Rink resin followed by further chlorine substitution, reduction of a nitro group and appropriate cyclization afforded benzimidazoles, benzotriazoles, quinoxalinones, benzodiazepinediones and succinimides. The method developed is suitable for the synthesis of diverse libraries including the mentioned types of heterocycles, which have significant importance in current drug discovery. In this paper, we also report limitation of these method and unsuccessful attempt to prepare an 8-membered benzodiazocine cycle.