Synthesis of triazolo-fused benzoxazepines and benzoxazepinones via Passerini reactions followed by 1,3-dipolar cycloadditions

被引：12

作者：

De Moliner, Fabio ^{[1
]}

Bigatti, Martina ^{[1
]}

De Rosa, Chiara ^{[1
]}

Banfi, Luca ^{[1
]}

Riva, Renata ^{[1
]}

Basso, Andrea ^{[1
]}

机构：

[1] Univ Genoa, Dept Chem & Ind Chem, I-16146 Genoa, Italy

来源：

MOLECULAR DIVERSITY | 2014年 / 18卷 / 03期

关键词：

Benzoxazepines; Benzoxazepinones; Azidoaldehydes; Multicomponent reactions; MCRs; Passerini reaction; Dipolar cycloaddition; Microwaves; MULTICOMPONENT REACTIONS; ACID; ISOCYANIDES; DERIVATIVES; ALDEHYDES; ALCOHOLS; UGI;

D O I：

10.1007/s11030-014-9530-x

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

Azidobenzaldehydes can be used in Passerini three-component condensations to synthesize small collections of triazolo-fused heterocycles in an efficient and combinatorial fashion upon post-condensation azide-alkyne cycloadditions. Triazolo-fused benzoxazepinones were obtained in moderate to good overall yields with a concise two-step protocol. Triazolo-fused benzoxazepines were instead prepared by means of a longer, yet straightforward route comprising a Passerini reaction, hydrolysis of the ester moiety, O-alkylation with propargylic bromides, and 1,3-dipolar cycloaddition.

引用

页码：473 / 482

页数：10

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