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A Novel and Efficient Synthesis of 3‐[(4,5‐Dihydro‐1 H ‐pyrrol‐3‐yl)carbonyl]‐2 H ‐chromen‐2‐ones (=3‐[(4,5‐Dihydro‐1 H ‐pyrrol‐3‐yl)carbonyl]‐2 H ‐1‐benzopyran‐2‐ones)
Author(s) -
Alizadeh Abdolali,
Ghanbaripour Rashid
Publication year - 2013
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.201200216
Subject(s) - chemistry , benzylamine , salicylaldehyde , coumarin , benzopyran , medicinal chemistry , stereochemistry , proton nmr , organic chemistry , schiff base
An efficient one‐pot synthesis of 3‐[(4,5‐dihydro‐1 H ‐pyrrol‐3‐yl)carbonyl]‐2 H ‐chromen‐2‐one (=3‐[(4,5‐dihydro‐1 H ‐pyrrol‐3yl)carbonyl]‐2 H ‐1‐benzopyran‐2‐one) derivatives 4 by a four‐component reaction of a salicylaldehyde 1 , 4‐hydroxy‐6‐methyl‐2 H ‐pyran‐2‐one, a benzylamine 2 , and a diaroylacetylene (=1,4‐diarylbut‐2‐yne‐1,4‐dione) 3 in EtOH is reported. This new protocol has the advantages of high yields ( Table ), and convenient operation. The structures of these coumarin (=2 H ‐1‐benzopyran‐2‐one) derivatives, which are important compounds in organic chemistry, were confirmed spectroscopically (IR, 1 H‐ and 13 C‐NMR, and EI‐MS) and by elemental analyses. A plausible mechanism for this reaction is proposed ( Scheme 2 ).