A NOVEL FURAN RING CONSTRUCTION AND SYNTHESES OF 4-SUBSTITUTED AND 4,5-SUBSTITUTED 2-(ALPHA-HETEROCYCLOALKYL)FURANS

被引：36

作者：

KATRITZKY, AR

LI, JQ

机构：

[1] Center for Heterocyclic Compounds, Department of Chemistry, University of Florida, Gainesville, Florida 32611-7200

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1995年 / 60卷 / 03期

关键词：

D O I：

10.1021/jo00108a028

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

4-Substituted and 4,5-disubstituted 2-(benzotriazol-1-ylmethyl)furans 3 have been prepared in good yields from 1-propargylbenzotriazole (1) and alpha-bromo ketones via one-pot processes. The 2(benzotriazol-1-ylmethyl) side chain of 3 was alkylated by lithiation followed by quenching with electrophiles to afford 4- and 4,5-substituted 2-(alpha-benzotriazol-1-ylalkyl)furans 11. Substitution of the benzotriazolyl groups of 3 and 11 with other heterocycles in the presence of ZnClB2 gave a variety of 4- and 4,5-substituted 2-(alpha-heterocycloalkyl)furans 10 and 12 in good yields.

引用

页码：638 / 643

页数：6

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