Skeletal Reorganization: Approaches towards the Synthesis of Aza-Heterocyclic Cores

Dedicated to Prof. Brindaban C. Ranu on the occasion of his 75^th birth anniversary

Abstract

The impetuous development of the pharmaceutical industry and material science stimulates the search for new synthetic approaches and new methods for the synthesis and functionalization of aza-heterocycles; these are some of the key objectives of modern organic chemistry. As a result, an advanced method towards the synthesis of functionalized N-heterocycles that circumvents the limitations associated with traditional methods needs to be devised. In recent decades, rearrangement/reorganization reactions have emerged as a powerful tool for the efficient synthesis of the aza-heterocycle. In this illustration, we summarize some our recent efforts in the development of few complex aza-heterocyclic cores.

1 Introduction

2 Skeletal Rearrangement of Small Heterocycles via Domino Ring-Opening and Ring-Closing (DROC) Strategy

3 Ru(II)-Catalyzed Skeletal Rearrangement of the Quinazoline Ring

4 Lewis Acid Catalyzed Skeletal Rearrangement of Furans to Indolizine Cores

5 Skeletal Rearrangement of Donor–Acceptor Cyclopropanes via Domino Ring-Opening and Ring-Closing (DROC) Strategy

6 Lewis Acid Mediated Skeletal Rearrangement of Donor–Acceptor Spirocyclopropylpyrazolones

7 Skeletal Rearrangement through Ring Distortion Strategy

8 Conclusion

Key words

reorganization approach - Brønsted acid - Lewis acid - 1H-azidirine - 2-pyridone - indolizine nucleus

Publication History

Received: 29 June 2024

Accepted after revision: 12 August 2024

Accepted Manuscript online:
12 August 2024

Article published online:
12 September 2024

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