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Synthesis and Elimination Pathways of 1-Methanesulfonyl-1,2-dihydroquinoline Sulfonamides.

ABSTRACT: A series of new Morita-Baylis-Hillman acetates were prepared and reacted with methanesulfonamide (K₂CO₃, DMF, 23 °C) to produce tertiary dihydroquinoline sulfonamides in high yields. Subsequent efforts to eliminate the methylsulfonyl group from these derivatives (K₂CO₃, DMF, 90 °C) as a route to quinolines were met with mixed results. Although dihydroquinoline sulfonamides prepared from ethyl acrylate and acrylonitrile generally underwent elimination to give excellent yields of quinolines, those generated from 3-buten-2-one failed to undergo elimination and instead decomposed. The failure of these ketone substrates to aromatize presumably derives from the enolizable methyl ketone at C-3. Finally, the attempted aromatization of the acrylate-derived 6,7-difluoro-1,2-dihydroquinoline sulfonamide demonstrated that other interesting processes could occur in preference to the desired elimination.

SUBMITTER: Ametsetor E

PROVIDER: S-EPMC10096818 | biostudies-literature | 2023 Apr

REPOSITORIES: biostudies-literature

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Synthesis and Elimination Pathways of 1-Methanesulfonyl-1,2-dihydroquinoline Sulfonamides.

Ametsetor Ebenezer E Fobi Kwabena K Bunce Richard A RA

Molecules (Basel, Switzerland) 20230405 7

A series of new Morita-Baylis-Hillman acetates were prepared and reacted with methanesulfonamide (K2CO3, DMF, 23 °C) to produce tertiary dihydroquinoline sulfonamides in high yields. Subsequent efforts to eliminate the methylsulfonyl group from these derivatives (K2CO3, DMF, 90 °C) as a route to quinolines were met with mixed results. Although dihydroquinoline sulfonamides prepared from ethyl acrylate and acrylonitrile generally underwent elimination t ...[more]

PMID: 37050020

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