通过多功能的 Passerini 型缩合反应，从醛类化合物出发，简便地制备侧链功能化聚（α-羟基酸）共聚物。

Facile procedure for generating side chain functionalized poly(alpha-hydroxy acid) copolymers from aldehydes via a versatile Passerini-type condensation.

机构信息

Department of Chemistry and Biochemistry, University of California, San Diego, 9500 Gilman Drive, La Jolla, California 92093-0358, USA.

出版信息

Org Lett. 2010 Aug 6;12(15):3560-3. doi: 10.1021/ol101433v.

DOI:10.1021/ol101433v

PMID:20608664

Abstract

A general method for synthesizing alpha-hydroxy N-acylindoles in one-pot via an acid-catalyzed condensation of a convertible isonitrile with water and various aldehydes is presented. These intermediates were incorporated into poly(alpha-hydroxy acid) copolymers bearing residues with functionalizable side chains, which could be further modified through Cu(I)-catalyzed azide-alkyne cylcoaddition reactions. This versatile synthetic strategy provides access to side chain functionalized poly(alpha-hydroxy acid) copolymers from readily available aldehydes, making it potentially useful as an approach to synthesize biodegradable polymers with new, tunable properties.

摘要

本文提出了一种通过酸催化可转化异腈与水和各种醛的缩合反应一锅法合成α-羟基 N-酰基吲哚的通用方法。这些中间体被掺入带有可功能化侧链的聚（α-羟基酸）共聚物中，这些侧链可以通过 Cu（I）-催化的叠氮-炔环加成反应进一步修饰。这种多功能的合成策略为从易得的醛制备侧链功能化的聚（α-羟基酸）共聚物提供了途径，这使其可能成为合成具有新的可调性能的可生物降解聚合物的一种方法。