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Synthetic Strategy for Pyrazolo[1,5- a]pyridine and Pyrido[1,2- b]indazole Derivatives through AcOH and O 2-Promoted Cross-dehydrogenative Coupling Reactions between 1,3-Dicarbonyl Compounds and N-Amino-2-iminopyridines

Synthetic Strategy for Pyrazolo[1,5- a]pyridine and Pyrido[1,2- b]indazole Derivatives through AcOH and O 2-Promoted Cross-dehydrogenative Coupling Reactions between 1,3-Dicarbonyl Compounds and N-Amino-2-iminopyridines

Haider Behbehani, Hamada Mohamed Ibrahim

ACS Omega. 2019 Sep 4;4(12):15289-15303.

PMID: 31552376

Abstract:

An efficient method has been developed for the synthesis of uniquely substituted pyrazolo[1,5-a]pyridine and pyrido[1,2-b]indazole derivatives, which involves acetic acid and molecular oxygen promoted cross-dehydrogenative coupling reactions of respective β-ketoesters and β-diketones (like ethyl acetoacetate, ethyl benzoylacetate, methyl propionylacetate, acetylacetone, dimedone, 1,3-cyclohexanedione, and 1,3-cyclopentanedione) with N-amino-2-iminopyridines. The proposed tentative mechanism involves formal acetic acid-promoted oxidative C(sp3)-C(sp2) dehydrogenative coupling followed by dehydrative cyclization under a catalyst-free condition within high atom economy processes.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP94020	Ethyl benzoylacetate		94-02-0	Price

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