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Synthesis of Fused Spiropyrrolidine Oxindoles Through 1,3‐Dipolar Cycloaddition of Azomethine Ylides Prepared from Isatins and α‐Amino Acids with Heterobicyclic Alkenes
Author(s) -
Kumaran Subramani,
Saritha Rajendhiran,
Gurumurthy Palanivelu,
Parthasarathy Kanniyappan
Publication year - 2020
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.202000247
Subject(s) - azomethine ylide , cycloaddition , chemistry , decarboxylation , aromatization , 1,3 dipolar cycloaddition , ylide , iminium , medicinal chemistry , organic chemistry , catalysis
The synthesis of various fused spiropyrrolidine oxindoles from isatins, amino acids, and heterobicyclic alkenes through a 1,3‐dipolar cycloaddition is described. For the first time, we used heterobicyclic alkenes as a dipolarophile in 1,3‐dipolar cycloaddition of the azomethine ylide generated by decarboxylation. Triflic acid mediated aromatization of cycloaddition products has been demonstrated. A possible mechanism is proposed that the formation of iminium carboxylate intermediate (I), azomethine ylide intermediate (II) via decarboxylation, subsequent 1,3‐dipolar cycloaddition with oxabenzonorbornadiene to give cycloaddition product.