Cyclodehydration and Baker-Venkataraman Rearrangement Methodologies for the Preparation of Fluorinated 4H-Chromones

Publish Year: 1399
نوع سند: مقاله ژورنالی
زبان: English
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JR_CHM-4-5_002

تاریخ نمایه سازی: 1 مرداد 1399

Abstract:

Trifluoromethylated and ring-fluorinated 4H-chromones have been prepared via cyclodehydration and via the baker-venkataraman rearrangement.  The cyclodehydration of 4,4,4-trifluoro-1-(1-naphthol-2-yl)-1,3-butanedione was performed under a variety of base promoted and acid catalyzed processes enroute to 2-trifluoromethyl-β-naphthochromone. Using microwave irradiative, sonication and conventional processes, selected o-hydroxyaromatic ketones underwent single-pot, based promoted baker-venkataraman rearrangements with trifluoroacetic anhydride to give trifluoromethylated 4H-chromones in yields ranging from 50-82%. Microwave irradiation conditions allowed for yields ranging from 50-80%, which compare favorably to yields achieved via conventional methods (60-82%) as well as reducing reaction times by 55% compared to conventional refluxing conditions.

Authors

Chloe Fernandes

School of Science and Technology, Georgia Gwinnett College, ۱۰۰۰ University Center Lane, Lawrenceville, G.A. ۳۰۰۴۳, USA

Sang H. Park

School of Science and Technology, Georgia Gwinnett College, ۱۰۰۰ University Center Lane, Lawrenceville, G.A. ۳۰۰۴۳, USA

Joseph Sloop

School of Science and Technology, Georgia Gwinnett College, ۱۰۰۰ University Center Lane, Lawrenceville, G.A. ۳۰۰۴۳, USA

Karla Wilmott

School of Science and Technology, Georgia Gwinnett College, ۱۰۰۰ University Center Lane, Lawrenceville, G.A. ۳۰۰۴۳, USA

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