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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.

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Publication details

The article was received on 08 Apr 2018, accepted on 11 Jun 2018 and first published on 12 Jun 2018


Article type: Paper
DOI: 10.1039/C8GC01099D
Citation: Green Chem., 2018, Accepted Manuscript
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    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, Accepted Manuscript , DOI: 10.1039/C8GC01099D

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