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An Efficient Synthesis of Chromeno[2,3‐ d ]pyrimidine‐2,4‐diones with a Nitroketene‐Aminal Moiety at C(5) by a One‐Pot Four‐Component Reaction
Author(s) -
Alizadeh Abdolali,
Ghanbaripour Rashid,
Weng Ng Seik
Publication year - 2015
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.201400276
Subject(s) - chemistry , aminal , moiety , barbituric acid , pyrimidine , component (thermodynamics) , stereochemistry , combinatorial chemistry , crystal structure , organic chemistry , physics , thermodynamics
An efficient and novel synthesis of chromeno[2,3‐ d ]pyrimidine‐2,4‐dione derivatives with a nitroketene‐aminal moiety at C(5) via four‐component reaction of salicylaldehydes, barbituric acid, diamines, and 1,1‐bis(methylsulfanyl)‐2‐nitroethene in EtOH and in the presence of AcOH is reported. Easy performance, good yields, and easy purification are the main advantages of this method. All structures were confirmed by IR, MS, and 1 H‐ and 13 C‐NMR, and by X‐ray crystal‐structure analyses. A plausible mechanism for this type of reaction is proposed ( Scheme ).