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

[Image: see text] 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(sp(3))–C(sp(2)) dehydrogenative coupling followed by dehydrative cyclization under a catalyst-free condition within high atom economy processes.