Synthesis 2016; 48(13): 2009-2025
DOI: 10.1055/s-0035-1560440
short review
© Georg Thieme Verlag Stuttgart · New York

Photochemical Synthesis of Azaheterocycles

Gerald J. Tanoury*
Vertex Pharmaceuticals Incorporated, 50 Northern Avenue, Boston, MA 02210, USA   Email: jerry_tanoury@vrtx.com
› Author Affiliations
Further Information

Publication History

Received: 24 February 2016

Accepted after revision: 03 March 2016

Publication Date:
12 April 2016 (online)


Abstract

Synthetic organic photochemistry is a field that continues to offer unique routes to organic structures not typically accessed from thermal reactions. In this review, the photochemical synthesis of five-, six-, seven-, and eight-membered-ring azaheterocycles, as well as some aza-macrocycles, is discussed. The discussion will focus on methods where heterocycle formation occurs during or as a result of a photochemical event. Reaction mechanisms will be discussed also, as these provide a rationale for understanding the synthetic results.

1 Introduction

2 Five-Membered Rings

2.1 Cyclization Reactions

2.2 Cycloadditions

2.3 From Aromatic and Vinyl Azides

2.4 earrangements

2.5 Other Individual Methods

3 Six-Membered Rings

3.1 Cyclization Reactions

3.2 Isocyanide Insertions

3.3 Cycloadditions

4 Seven-Membered Rings and Larger

5 Conclusion