Premium
An Efficient Synthesis of 3‐(1 H‐ Tetrazol‐5‐yl)coumarins (=3‐(1 H ‐Tetrazol‐5‐yl)‐2 H ‐1‐benzopyran‐2‐ones) via Domino Knoevenagel Condensation, Pinner Reaction, and 1,3‐Dipolar Cycloaddition in Water
Author(s) -
Tisseh Zeinab Noroozi,
Dabiri Minoo,
Bazgir Ayoob
Publication year - 2012
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.201200031
Subject(s) - chemistry , sodium azide , malononitrile , knoevenagel condensation , cycloaddition , coumarin , domino , medicinal chemistry , benzopyran , organic chemistry , combinatorial chemistry , stereochemistry , catalysis
A novel straightforward synthesis of 3‐(1 H ‐tetrazol‐5‐yl)coumarins (=3‐(1 H ‐tetrazol‐5‐yl)‐2 H ‐1‐benzopyran‐2‐ones) 6 via domino Knoevenagel condensation, Pinner reaction, and 1,3‐dipolar cycloaddition of substituted salicylaldehydes (=2‐hydroxybenzaldehydes), malononitrile (propanedinitrile), and sodium azide in H 2 O is reported ( Scheme 1 and Table 2 ). This general protocol provides a wide variety of 3‐(1 H ‐tetrazol‐5‐yl)coumarins in good yields under mild reaction conditions.