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A Novel and Efficient Synthesis of Pyrido[1,2‐ a ]‐Fused 1,3‐Diazaheterocyclic Compounds via a One‐Pot Three‐Component Reaction
Author(s) -
Alizadeh Abdolali,
Rezvanian Atieh
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.201100274
Subject(s) - chemistry , component (thermodynamics) , elemental analysis , proton nmr , combinatorial chemistry , aqueous solution , organic chemistry , stereochemistry , medicinal chemistry , thermodynamics , physics
An efficient one‐pot synthesis of pyrido[1,2‐ a ]‐fused 1,3‐diazaheterocyclic compounds by three‐component reaction of diamine, nitroketene dithioacetal (=1,1‐bis(methylsulfanyl)‐2‐nitroethene), and electron‐poor itaconic anhydride (=2‐methylidenesuccinic anhydride=2‐methylidenebutanedioic anhydride) in aqueous EtOH is reported. This protocol has the advantages of easiness, higher yields, and shorter reaction times. The structures were corroborated spectroscopically (IR, 1 H‐ and 13 C‐NMR, and EI‐MS) and by elemental analyses. A plausible mechanism for this type of cyclization is proposed ( Scheme 2 ).