A Highly Regio and Stereoselective Synthesis of (Z)-3-Aryl(alkyl)idene Isoindolin-1-ones via Palladium Catalyzed Annulation of Terminal Alkynes

M. Wahab Khan; Nitya G. Kundu

doi:10.1055/s-1997-1049

Synlett 1997; 1997(12): 1435-1437
DOI: 10.1055/s-1997-1049

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A Highly Regio and Stereoselective Synthesis of (Z)-3-Aryl(alkyl)idene Isoindolin-1-ones via Palladium Catalyzed Annulation of Terminal Alkynes

M. Wahab Khan, Nitya G. Kundu^*

^*Department of Organic Chemistry, Indian Association for the Cultivation of Science, Jadavpur, Calcutta 700 032, India, Fax: (91) (33) 473 2805; e-mail: ocngk@iacs.ernet.in

Abstract

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o-Iodobenzamide or its N-substituted derivatives 4-10 and terminal alkynes 11-17 reacted in DMF in the presence of bis(triphenylphosphine)palladium(II)chloride, cuprous iodide and triethylamine leading to (Z)-3-arylidene isoindolin-1-ones (22, 24, 27 and 28) or o-alkynyl N-substituted benzamides (I). The latter could be cyclised with sodium in ethanol in a completely regio and stereoselective manner to (Z)-3-aryl(alkyl)idene isoindolin-1-ones 18-35.

palladium-catalysis - heteroannulation - isoindolinones - phthalimidines

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