[4+n] Annulation Reactions Using ortho-Chloromethyl Anilines as Aza-ortho-Quinone Methide Precursors

Abstract

Aza-ortho-quinone methides are important reactive intermediates that have found broad applications in synthetic chemistry. Recently, 1,4-elimination of ortho-chloromethyl aniline derivatives has emerged as a novel, powerful and convenient method for aza-ortho-quinone methide generation. This review will highlight the recent applications of aza-ortho-quinone methide precursors in annulation reactions to access various biologically important nitrogen-containing heterocycles. The general mechanisms are briefly discussed as well.

1 Introduction

2 [4+n] Annulation Reactions Using ortho-Chloromethyl Anilines as Aza-ortho-Quinone Methide Precursors

2.1 [4+2] Annulation Reactions

2.2 [4+1] Annulation Reactions

2.3 [4+3] Annulation Reactions

3 Conclusion and Perspective

Key words

annulation - nitrogen-containing heterocycles - aza-ortho-quinone methides - ortho-chloromethyl anilines - 4-atom units

Publication History

Received: 27 May 2021

Accepted after revision: 16 June 2021

Accepted Manuscript online:
16 June 2021

Article published online:
27 July 2021

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