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Two Different Green Catalytic Systems for One‐Pot Regioselective and Chemoselective Synthesis of Some Pyrimido[4,5‐ d ]Pyrimidinone Derivatives in Water
Author(s) -
Rimaz Mehdi,
Khalafy Jabbar,
Mousavi Hossein,
Bohlooli Sanaz,
Khalili Behzad
Publication year - 2017
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.2932
Subject(s) - chemistry , regioselectivity , chemoselectivity , thiourea , catalysis , pyrimidine , organic chemistry , dabco , combinatorial chemistry , condensation , heteroatom , stereochemistry , alkyl , physics , thermodynamics
In this work, we have developed green and efficient regioselective and chemoselective syntheses of 5‐aryloyl‐1,3‐dimethyl‐7‐thioxo‐5,6,7,8‐tetrahydropyrimido[4,5‐ d ]pyrimidine‐2,4(1 H ,3 H )‐dione and 5‐aryloyl‐1,3‐dimethyl‐2,7‐dithioxo‐2,3,5,6,7,8‐hexahydropyrimido[4,5‐ d ]pyrimidin‐4(1 H )‐one derivatives via one‐pot three‐component Biginelli‐like condensation of arylglyoxal monohydrates, N , N ‐dimethylbarbituric acid or N , N ‐dimethyl‐2‐thiobarbituric acid, and thiourea in water at 50°C. The presence of two different green catalytic systems (ZrOCl 2 .8H 2 O and also DABCO) proceeded efficiently to afford the desired products in good‐to‐excellent yields. An aqueous reaction medium, high regioselectivity and chemoselectivity, simple operation and suitable yields of products are the important features of these green protocols.