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p ‐Toluenesulfonic Acid‐Mediated Three‐Component Reaction “On‐Water” Protocol for the Synthesis of Novel Thiadiazolo[2,3‐ b ]quinazolin‐6(7 H )‐ones
Author(s) -
Wadhwa Preeti,
Kaur Tanpreet,
Singh Neetu,
Singh Udai P.,
Sharma Anuj
Publication year - 2016
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201500397
Subject(s) - chemistry , p toluenesulfonic acid , combinatorial chemistry , microwave irradiation , aryl , functional group , medicinal chemistry , stereochemistry , organic chemistry , catalysis , alkyl , polymer
The first p ‐toluenesulfonic acid‐mediated “on‐water” multicomponent reaction sequence for the synthesis of novel thiadiazolo[2,3‐ b ]quinazolinones from 5‐aryl‐1,3,4‐thiadiazol‐2‐amines, cyclic 1,3‐dicarbonyls and aldehydes with microwave irradiation is described. This protocol proceeds with high atom economy and leads to the generation of three rings, together with one C−C, one C=N and two C−N bonds in a single operation. This new methodology has advantages such as operational simplicity, mild conditions, broad functional group tolerance, simple work‐up procedure and applicability on a gram scale.