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One‐Pot Three‐Component Synthesis of 2‐(Alkylimino)‐7‐oxo‐1‐oxa‐6‐azaspiro[4.4]nona‐3,8‐diene‐3,4‐dicarboxylates
Author(s) -
Adib Mehdi,
Moghimi Setareh,
Sayahi Mohammad Hosein,
Bijanzadeh Hamid Reza
Publication year - 2009
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.200800324
Subject(s) - chemistry , phthalimide , acetylenedicarboxylate , diene , isocyanide , yield (engineering) , component (thermodynamics) , dimethyl acetylenedicarboxylate , medicinal chemistry , organic chemistry , catalysis , cycloaddition , natural rubber , materials science , physics , metallurgy , thermodynamics
The reactive zwitterionic 1 : 1 intermediate 6 generated in situ from the reaction between an isocyanide 2 and a dialkyl acetylenedicarboxylate (=dialkyl but‐2‐ynedioate) 3 was trapped by an N ‐arylmaleimide or ‐phthalimide 4 to produce a highly functionalized 1‐oxa‐6‐azaspiro[4.4]nona‐3,8‐diene‐3,4‐dicarboxylate 5 in excellent yield ( Scheme and Table ).