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One‐Pot Synthesis of Dispiro[oxindole‐3,3′‐pyrrolidines] by Three‐Component [3+2] Cycloadditions of in situ ‐Generated Azomethine Ylides with 3‐Benzylidene‐2,3‐dihydro‐1 H ‐indol‐2‐ones
Author(s) -
Matloubi Moghaddam Firouz,
Kiamehr Mostafa,
Reza Khodabakhshi Mohammad,
Jebeli Javan Marjan,
Fathi Shaghayegh,
Villinger Alexander,
Iaroshenko Viktor O.,
Langer Peter
Publication year - 2013
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.201200602
Subject(s) - chemistry , sarcosine , oxindole , regioselectivity , decarboxylation , azomethine ylide , cycloaddition , in situ , catalysis , isatin , component (thermodynamics) , 1,3 dipolar cycloaddition , combinatorial chemistry , organic chemistry , amino acid , glycine , biochemistry , physics , thermodynamics
An efficient one‐pot, three‐component synthesis of novel dispiro[oxindole‐3,3′‐pyrrolidines] by 1,3‐dipolar cycloaddition of azomethine ylides, in situ generated by reaction of 1,2‐diones with sarcosine and subsequent decarboxylation, with a series of ( E )‐3‐benzylidene‐2,3‐dihydro‐1 H ‐indol‐2‐ones is reported. Molecular complexity is generated in only one synthetic step. All reactions proceed with excellent regioselectivity and in good‐to‐excellent yields. The workup is easy, the reaction times are short, and no catalyst is required.