利用异苯并呋喃-腈狄尔斯-阿尔德反应合成异喹啉的新方法。

Novel synthesis of isoquinolines using isobenzofuran-nitrile Diels-Alder reactions.

作者信息

Ghorai Binay K, Jiang Delu, Herndon James W

机构信息

Department of Chemistry and Biochemistry, New Mexico State University, MSC 3C, Las Cruces, New Mexico 88003, USA.

出版信息

Org Lett. 2003 Nov 13;5(23):4261-3. doi: 10.1021/ol035405d.

DOI:10.1021/ol035405d

PMID:14601975

Abstract

[reaction: see text] The synthesis of isoquinolines through coupling of 2-alkynylbenzaldehyde derivatives with beta-cyanocarbene complexes has been examined. The reaction involves formation of an isobenzofuran followed by intramolecular Diels-Alder reaction with the nitrile, a process with limited precedent. The unique success of this process in this system has been attributed to deoxygenation of the initial adduct to form the isoquinoline ring system.

摘要

[反应：见正文] 已对通过2-炔基苯甲醛衍生物与β-氰基卡宾配合物的偶联来合成异喹啉进行了研究。该反应涉及异苯并呋喃的形成，随后与腈进行分子内狄尔斯-阿尔德反应，这一过程先例有限。该过程在该体系中的独特成功归因于初始加合物的脱氧以形成异喹啉环系。