1,3-cycloaddition reactions of 2-oxo-2H-[1]benzopyran-4-carbonitrile N-oxide. Synthesis of several new 4-substituted coumarins
✍ Scribed by Demetrios N. Nicolaides; Konstantina C. Fylaktakidou; Konstantinos E. Litinas; George K. Papageorgiou; Dimitra J. Hadjipavlou-Litina
- Book ID
- 102892854
- Publisher
- Journal of Heterocyclic Chemistry
- Year
- 1998
- Tongue
- English
- Weight
- 527 KB
- Volume
- 35
- Category
- Article
- ISSN
- 0022-152X
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✦ Synopsis
Abstract
1,3‐Cycloaddition reactions of new 2‐oxo‐2__H__‐[1]benzopyran‐4‐carbonitrile N‐oxide 2 with dipolarophiles, o‐aminophenols and o‐phenylenediamine resulted in 4‐heterocyclic substituted coumarin derivatives. These derivatives are screened for antiinflammatory activity in vitro through their antiproteolytic activity, the interaction with 1,1‐diphenyl‐2‐picrylhydrazyl and the ability to affect superoxide anion and to inhibit β‐glucuronidase and soybean lipoxygenase.
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## Abstract magnified image The title aldehyde **1** reacts smoothly with the enamine moiety of **2**‐aminochromone **2** to produce hitherto unreported 3‐(2‐hydroxybenzoyl)‐5__H__‐1‐benzopyrano[2,3‐__b__]pyridin‐5‐one (azaxanthone) **5**. This reaction has been extended for the synthesis of bisaz