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Highly Convergent One‐Pot Four‐Component Regioselective Synthesis of Spiro‐pyranopyrazoles and Oxa‐aza‐[3.3.3]propellanes
Author(s) -
Alizadeh Abdolali,
Bayat Fahimeh
Publication year - 2014
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.201300260
Subject(s) - regioselectivity , chemistry , ninhydrin , malononitrile , hydrazine (antidepressant) , dimethyl acetylenedicarboxylate , component (thermodynamics) , combinatorial chemistry , organic chemistry , stereochemistry , computational chemistry , cycloaddition , biochemistry , physics , amino acid , chromatography , thermodynamics , catalysis
A concise and efficient route for the synthesis of spiro‐pyranopyrazoles and oxa‐aza‐[3.3.3]propellanes by simple regioselective multicomponent reaction of ninhydrin, malononitrile, hydrazine derivatives, and β ‐keto esters or dimethyl acetylenedicarboxylate was developed. This protocol provides an alternative method for combinatorial and parallel syntheses in drug discovery. The value of this method lies in its simplicity, regioselectivity, and good yields. The structures of 3 and 4 were corroborated spectroscopically (IR, 1 H‐ and 13 C‐NMR, and EI‐MS). A plausible mechanism for this type of reaction is proposed ( Schemes 2 and 3 ).