New efficient synthesis of polysubstituted 3,4-dihydroquinazolines and 4H-3,1-benzothiazines through a Passerini/Staudinger/aza-Wittig/addition/nucleophilic substitution sequence

被引：11
|
作者：
Zhao, Long [1 ]
Yang, Mao-Lin [1 ]
Liu, Min [1 ]
Ding, Ming-Wu [1 ]
机构：
[1] Cent China Normal Univ, Hubei Int Sci & Technol Cooperat Base Pesticide &, Minist Educ, Key Lab Pesticide & Chem Biol, Wuhan 430079, Peoples R China
来源：
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY | 2022年 / 18卷
基金：
中国国家自然科学基金;
关键词：
aza-Wittig reaction; 3,4-dihydroquinazoline; 4H-3,1-benzothiazine; nucleophilic substitution; Passerini reaction; Staudinger reaction; ONE-POT SYNTHESIS; BIOLOGICAL EVALUATION; DERIVATIVES; ACCESS;
D O I：
10.3762/bjoc.18.32
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A new efficient synthesis of polysubstituted 3,4-dihydroquinazolines and 4H-3,1-benzothiazines via sequential Passerini/Staudinger/aza-Wittig/addition/nucleophilic substitution reaction has been developed. The three-component Passerini reactions of 2-azidobenzaldehydes 1, benzoic acid (2), and isocyanides 3 produced the azide intermediates 4, which were treated sequentially with triphenylphosphine, isocyanates (or CS2), and secondary amines to give polysubstituted 3,4-dihydroquinazolines 8 and 4H-3,1-benzothiazines 11 in good overall yields through consecutive Passerini/Staudinger/aza-Wittig/addition/nucleophilic substitution reactions.
引用
收藏
页码：286 / 292
页数：7
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