5-取代5-氨基戊二烯醛的重排反应

Rearrangement of 5-Substituted 5-Aminopentadienals.

作者信息

Fischer Fabian, Berger Daniel, Neuenschwander Markus

机构信息

Departement für Chemie und Biochemie der Universität, Freiestrasse 3, CH-3012 Bern (Switzerland) Fax: (+41) 31-631-3426.

出版信息

Angew Chem Int Ed Engl. 1998 Aug 17;37(15):2138-2140. doi: 10.1002/(SICI)1521-3773(19980817)37:15<2138::AID-ANIE2138>3.0.CO;2-5.

DOI:10.1002/(SICI)1521-3773(19980817)37:15<2138::AID-ANIE2138>3.0.CO;2-5

PMID:29711043

Abstract

Strong nucleophiles are needed for inducing ring opening 3→4 since the pyrylium salt intermediates 3, formed from 5-X-substituted 5-aminopenta-2,4-dienals 2 upon treatment with acid, are quite unreactive due to "aromatic" stabilization. However, this allows an easy access to a variety of 2-aminopyrylium salts 3 from "push-pull" enynes 1. X=OAc, F, Cl, Br, I, OPh.

摘要

由于由5-X-取代的5-氨基戊-2,4-二烯醛2经酸处理形成的吡啶鎓盐中间体3因“芳香性”稳定而相当不活泼，所以开环3→4需要强亲核试剂。然而，这使得从“推-拉”烯炔1容易获得各种2-氨基吡啶鎓盐3。X = OAc、F、Cl、Br、I、OPh。