Issue 28, 2024

Leveraging in situ N-tosylhydrazones as diazo surrogates for efficient access to pyrazolo-[1,5-c]quinazolinone derivatives

Abstract

We developed a transition metal-free methodology for the construction of pyrazoloquinazolinone derivatives. The strategy involves a one-pot reaction wherein the N-tosylhydrazone and its corresponding diazo derivative are generated in situ, followed by an intramolecular 1,3-dipolar cycloaddition–ring expansion to provide the pyrazolo-[1,5-c]quinazolinone motif. This approach enables straightforward access to a diverse range of highly functionalized N-heterocyclic compounds in good yields (up to 92%).

Graphical abstract: Leveraging in situ N-tosylhydrazones as diazo surrogates for efficient access to pyrazolo-[1,5-c]quinazolinone derivatives

Supplementary files

Article information

Article type
Paper
Submitted
05 Jun 2024
Accepted
20 Jun 2024
First published
21 Jun 2024
This article is Open Access
Creative Commons BY-NC license

Org. Biomol. Chem., 2024,22, 5816-5821

Leveraging in situ N-tosylhydrazones as diazo surrogates for efficient access to pyrazolo-[1,5-c]quinazolinone derivatives

J. Yan, P. Retailleau, C. Tran and A. Hamze, Org. Biomol. Chem., 2024, 22, 5816 DOI: 10.1039/D4OB00950A

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