Issue 13, 2018

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

Abstract

A two-step method for the (3 + 2) cycloaddition of azomethine ylides followed by a double SN2 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.

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

Supplementary files

Article information

Article type
Paper
Submitted
08 Apr 2018
Accepted
11 Jun 2018
First published
12 Jun 2018

Green Chem., 2018,20, 3134-3139

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

A. Muthengi, X. Zhang, G. Dhawan, W. Zhang, F. Corsini and W. Zhang, Green Chem., 2018, 20, 3134 DOI: 10.1039/C8GC01099D

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