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

Green Chemistry Pub Date: 2018-06-12 DOI: 10.1039/C8GC01099D

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
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