Regiospecific generation and application of 3-lithiomethyl-2-methyl-1-phenylpyrazolin-5-one as 1,3-binucleophile in aromatic annelation: a novel approach for synthesis of 1,2-disubstituted indazolones and their condensed analogs

Reddy, Kethiri R. ; Roy, Amrita ; Ila, Hiriyakkanavar ; Junjappa, Hiriyakkanavar (1995) Regiospecific generation and application of 3-lithiomethyl-2-methyl-1-phenylpyrazolin-5-one as 1,3-binucleophile in aromatic annelation: a novel approach for synthesis of 1,2-disubstituted indazolones and their condensed analogs Tetrahedron, 51 (40). pp. 10941-10952. ISSN 0040-4020

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Official URL: http://linkinghub.elsevier.com/retrieve/pii/004040...

Related URL: http://dx.doi.org/10.1016/0040-4020(95)00650-W

Abstract

The enolate anion 5A generated by deprotonation of 2,3-dimelhyl- 1-phenylpyrazolin-5-one is shown to undergo highly regioselective γ-1,4-addition to α-oxoketene dithioacelals followed by cycloaromatizalion in the presence of boron trifluoride etherate to afford wide range of novel substituted and condensed indazolones in good yields.

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