Photomediated Radical Cascade Addition–Cyclization of N-Butenoyl Tetrahydroquinolines: Accessing Functionalized Julolidines DOI

Ajal P. Shaji,

Naremaddepalli S. Sudarshan,

Burkhard Koenig

et al.

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: April 14, 2025

Herein, we describe the photomediated radical cascade addition-cyclization of N-butenoyl tetrahydroquinolines to access various functionalized julolidine-5-one. The scope methodology was illustrated with several sulfonyl chlorides and tetrahydroquinolines. Other precursors, such as trifluoromethyl, bromoacetonitrile, bromoacetates, etc., also worked efficiently, demonstrating broad utility method. Finally, large-scale synthesis sulfonyl-substituted julolidine-5-one downstream conversions synthesized julolidine derivatives were carried out illustrate synthetic methodology.

Language: Английский

Photomediated Radical Cascade Addition–Cyclization of N-Butenoyl Tetrahydroquinolines: Accessing Functionalized Julolidines DOI

Ajal P. Shaji,

Naremaddepalli S. Sudarshan,

Burkhard Koenig

et al.

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: April 14, 2025

Herein, we describe the photomediated radical cascade addition-cyclization of N-butenoyl tetrahydroquinolines to access various functionalized julolidine-5-one. The scope methodology was illustrated with several sulfonyl chlorides and tetrahydroquinolines. Other precursors, such as trifluoromethyl, bromoacetonitrile, bromoacetates, etc., also worked efficiently, demonstrating broad utility method. Finally, large-scale synthesis sulfonyl-substituted julolidine-5-one downstream conversions synthesized julolidine derivatives were carried out illustrate synthetic methodology.

Language: Английский

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