Sequential (3+2) cycloaddition and (5+n) annulation for modular synthesis of dihydrobenzoxazines, tetrahydrobenzoxazepines and tetrahydrobenzoxazocines

被引：27

作者：

Muthengi, Alex ^{[1
,2
]}

Zhang, Xiaofeng ^{[1
,2
]}

Dhawan, Gagan ^{[3
]}

Zhang, Wensheng ^{[4
]}

Corsini, Francesca ^{[1
,2
]}

Zhang, Wei ^{[1
,2
]}

机构：

[1] Univ Massachusetts, Dept Chem, 100 Morrissey Blvd, Boston, MA 02125 USA

[2] Univ Massachusetts, Ctr Green Chem, 100 Morrissey Blvd, Boston, MA 02125 USA

[3] Univ Delhi, Dept Biomed Sci, Acharya Narendra Dev Coll, New Delhi 110019, India

[4] Jiaozuo Teachers Coll, Sch Sci & Technol, Jiaozuo 454100, Peoples R China

来源：

GREEN CHEMISTRY | 2018年 / 20卷 / 13期

关键词：

GREEN CHEMISTRY; ONE-POT; PHARMACEUTICAL-INDUSTRY; AZOMETHINE YLIDES; 1,3-DIPOLAR CYCLOADDITION; STEREOSELECTIVE-SYNTHESIS; DIPOLAR CYCLOADDITIONS; HETEROCYCLIC SCAFFOLDS; CHEMICAL-PROCESSES; ORGANIC-SYNTHESIS;

D O I：

10.1039/c8gc01099d

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A two-step method for the (3 + 2) cycloaddition of azomethine ylides followed by a double S(N)2 substitution-based (5 + n) annulation is introduced for the modular synthesis of dihydrobenzoxazine, tetrahydrobenzoxazepine and tetrahydrobenzoxazocine derivatives. After a quick water wash without further purification, the (3 + 2) cycloaddition intermediates were used for the (5 + n) annulation to afford products. Green chemistry metrics analysis of the synthetic processes provided favorable results.

引用

页码：3134 / 3139

页数：6

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