Copper-catalysed dehydrogenative self-coupling/cyclization of 5-aminopyrazoles: synthesis and photophysical study of pyridazines

An interesting self-coupling/cyclization of 5-aminopyrazoles is revealed, which provides a variety of pyridazine cores in reasonable yields. In this reaction, C(sp 2 )-C(sp 2 ) and N-N bond formation occurs simultaneously in one reaction vessel. The photophysical properties of the synthesized compou...

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Bibliographic Details
Published in:Chemical communications (Cambridge, England) England), 2023-08, Vol.59 (63), p.9642-9645
Main Authors: Rastogi, Gaurav K, Deb, Mohit L, Baruah, Pranjal K
Format: Article
Language:English
Subjects:
Coupling
Dehydrogenation
Pyridazines
Reaction mechanisms
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Summary:An interesting self-coupling/cyclization of 5-aminopyrazoles is revealed, which provides a variety of pyridazine cores in reasonable yields. In this reaction, C(sp 2 )-C(sp 2 ) and N-N bond formation occurs simultaneously in one reaction vessel. The photophysical properties of the synthesized compounds were also studied and some of them exhibited fluorescence properties with good quantum yields. A radical mediated reaction mechanism is proposed with the help of control experiments. One pot synthesis of the pyridazine core from 5-aminopyrazoles through C(sp 2 )-C(sp 2 ) and N&z.dbd;N bond formation.
ISSN:1359-7345
1364-548X
DOI:10.1039/d3cc02424e