A facile synthetic route to 1,1-disubstituted 2,3-dihydro-1H-benz[f]indene-4,9-diones

Pal, Sitaram ; Banik, Bimal K. ; Ghatak, Usha Ranjan (1992) A facile synthetic route to 1,1-disubstituted 2,3-dihydro-1H-benz[f]indene-4,9-diones Synthesis (11). pp. 1073-1075. ISSN 0039-7881

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Official URL: https://www.thieme-connect.com/ejournals/abstract/...

Related URL: http://dx.doi.org/10.1055/s-1992-26304

Abstract

A facile synthetic route is described for 1,1-dimethyl and 1-methoxy-carbonyl-1-methyl substituted 2,3-dihydro-1H-benz[f]indene-4,9-diones 7a, 7c and 7d from the corresponding 1,2,3,4-tetrahydrofluorenes 2a, 2c, and 2d involving ruthenium-catalyzed periodate oxidation of the tetrasubstituted double bond to the respective 6,7,8,9,10,11-hexahydro-5,10-dioxo-5H-benzocyclononenes 3a, 3c and 3d, cyclization-dehydration (aromatization) and methylation to 2,3-dihydro-4-methoxy-1H-benz[f]indenes 6a, 6c and 6d, followed by oxidation with pyridinium chlorochromate/Celite. The only exception to this trend is 2b, which on ruthenium-catalyzed Periodate oxidation directly affords 7b.

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