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One‐Pot Synthesis of 4‐(2,3‐Dihydro‐2‐hydroxy‐1,3‐dioxo‐1 H ‐inden‐2‐yl)‐Substituted 1‐Aryl‐1 H ‐pyrazole‐3‐carboxylates via a Tandem Three‐Component Reaction
Author(s) -
Alizadeh Abdolali,
Zarei Ameneh,
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.201100317
Subject(s) - chemistry , ninhydrin , pyrazole , aryl , domino , catalysis , cascade reaction , medicinal chemistry , stereochemistry , combinatorial chemistry , organic chemistry , biochemistry , alkyl , amino acid
The hitherto unreported, highly functionalized 1 H ‐pyrazole‐3‐carboxylates 3 have been synthesized in good yields via a one‐pot three‐component domino reaction of phenylhydrazines, dialkyl acetylenedicarboxylates, and ninhydrin under mild conditions for the first time. No co‐catalyst or activator is required for this multicomponent reaction, and the reaction is, from an experimental point of view, simple to perform ( Scheme 1 ). The structures of compounds 3 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/addition reaction is proposed ( Scheme 2 ).