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A convenient one-pot synthesis of new 3-(4-aryl-5-oxo-5,6,7,8-tetrahydro-4H-chromen-2-yl)-2H-chromen-2-ones

✍ Scribed by V. Rajeswar Rao; V. Ravinder Reddy

Publisher
Journal of Heterocyclic Chemistry
Year
2007
Tongue
English
Weight
229 KB
Volume
44
Category
Article
ISSN
0022-152X

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✦ Synopsis

Abstract

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Anhydrous zinc bromide catalysed reactions of arylidine‐3‐acetyl coumarins (1a‐c) and 5,6‐benzoanalogs of arylidine 3‐acetyl coumarins (4a,4b) with 1,3‐cyclohexanedione gives ‐(4‐aryl‐5‐oxo‐5,6,7,8‐tetrahydro‐4__H__‐chromen‐2yl)‐2__H__‐chromen‐2‐ones (3a, 3c) and 5,6‐benzoanalogs of 3‐(4‐aryl‐5‐oxo‐5,6,7,8‐tetrahydro‐4__H__‐chromen‐2yl)‐2__H__‐chromen‐2‐one (5a,5b). Under similar conditions arylidine‐3‐acetylcoumarins (1a, 1b,1d, 1e, 1f) and 5,6‐benzoanalog of arylidine 3‐acetyl coumarin (4b) react with 5,5‐dimethyl‐1,3‐cyclohexanedione (dimedone) yielding 3‐(4‐aryl‐7,7‐dimethyl‐5‐oxo‐5,6,7,8‐tetrahydro‐4__H__‐chromen‐2‐yl)‐2__H__‐chromen‐2‐ones (3d‐3h) and the 5,6‐benzoanalog of 3.(4‐aryl‐7,7‐dimethyl‐5‐oxo‐5,6,7,8‐tetrahydro‐4__H__‐chromen‐2‐yl)‐2__H__‐chromen‐2‐one (5c).

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An easy, simple and versatile one step synthesis of 3-(2-oxo-2H-chromen-3-yl)-6H,8H-pyrimido[4,5-c]pyridazine-5,7-diones is reported by reaction of 3-acetylcoumarins (1) with alloxan monohydrate (2) in acetic acid followed by hydrazine hydrate.