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Synthesis 2017; 49(20): 4562-4585
DOI: 10.1055/s-0036-1590859
short review
© Georg Thieme Verlag Stuttgart · New York

An Update on Direct C–H Bond Functionalization of Nitrogen-Containing Fused Heterocycles

Jessy Aziz
a   Institut Curie, PSL Research University, CNRS, INSERM, UMR9187-U1196, 91405, Orsay, France
,
Sandrine Piguel*
a   Institut Curie, PSL Research University, CNRS, INSERM, UMR9187-U1196, 91405, Orsay, France
b   Université Paris Sud, Université Paris-Saclay, 91405, Orsay, France   Email: sandrine.piguel@u-psud.fr
› Author Affiliations
Further Information

Publication History

Received: 28 June 2017

Accepted: 06 July 2017

Publication Date:
25 August 2017 (online)

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Abstract

This report highlights the recent advances in direct C–H bond functionalization of 5,5- and 6,5-fused heterocycles containing at least two nitrogen atoms. Besides C–C bond formation, C–N, C–S, C–P, and C–Si bonds can also be created via a metal-catalyzed process. Some examples, where a C–H functionalization approach was applied for the synthesis of drug candidates, will be presented as well.

1 Introduction

2 C–H Functionalization Reactions of N-Containing Heterocycles

2.1 Imidazo[1,2-a]pyridines

2.2 Pyrrolo[1,2-a]pyrazines

2.3 Imidazo[1,2-b]pyrazoles

2.4 Imidazo[1,2-a]pyrimidines

2.5 Imidazo[1,2-a]pyrazines and Imidazo[1,5-a]pyrazines

2.6 Imidazo[1,2-b]pyridazines

2.7 Imidazo[4,5-b]pyridines and Imidazo[4,5-c]pyridines

2.8 Pyrazolo[3,4-b]pyridines

2.9 Pyrazolo[1,5-a]pyrimidines

2.10 Pyrrolo[2,3-d]pyrimidines and Pyrrolo[3,2-d]pyrimidines

2.11 Imidazo[1,2-b][1,2,4]triazines

2.12 Imidazo[1,2-b][1,2,4,5]tetrazines

3 Outlook

4 Conclusion

Key words

heterocycles - nitrogen - C–H bond - direct functionalization - catalysis - regioselectivity