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

Xiao-Yu He; Yu-Hong Ma; Qing-Qing Yang; Wen-Jing Xiao

doi:10.1055/a-1529-7739

Synthesis 2022; 54(04): 953-964
DOI: 10.1055/a-1529-7739

special topic

Cycloadditions – Established and Novel Trends – in Celebration of the 70th Anniversary of the Nobel Prize Awarded to Otto Diels and Kurt Alder

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

Xiao-Yu He

^aCollege of Materials and Chemical Engineering, Key Laboratory of Inorganic Nonmetallic Crystalline and Energy Conversion Materials, China Three Gorges University, Yichang, Hubei 443002 P. R. of China

,

Yu-Hong Ma

^aCollege of Materials and Chemical Engineering, Key Laboratory of Inorganic Nonmetallic Crystalline and Energy Conversion Materials, China Three Gorges University, Yichang, Hubei 443002 P. R. of China

,

Qing-Qing Yang∗

^aCollege of Materials and Chemical Engineering, Key Laboratory of Inorganic Nonmetallic Crystalline and Energy Conversion Materials, China Three Gorges University, Yichang, Hubei 443002 P. R. of China

,

Wen-Jing Xiao ∗

^bKey Laboratory of Pesticide & Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University, 152 Luoyu Road, Wuhan, Hubei 430079 P. R. of China

› Institutsangaben

Abstract

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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

Volltext

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