Premium
Regioselective synthesis of novel spiroheterocyclic framework via the 1,3‐dipolar cycloaddition
Author(s) -
Hu Xiaofen,
Feng Yaqing,
Qiao Kangjian,
Zhou Weiyi
Publication year - 2006
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570430112
Subject(s) - regioselectivity , chemistry , isatin , sarcosine , cycloaddition , pyrrolidine , oxindole , 1,3 dipolar cycloaddition , azomethine ylide , ring (chemistry) , pyrimidine , stereochemistry , combinatorial chemistry , organic chemistry , catalysis , amino acid , glycine , biochemistry
A series of novel dispiro[oxindole‐fused pyrimidine]pyrrolidine ring systems 4a‐f were synthesized by the regioselective 1,3‐dipolar cycloaddition reaction of the 2‐arylmethylene‐7‐benzyl‐9‐(benzylidene)tetrahydropyrido[4,3‐ d ]thiazolo[3,2‐ a ]pyrimidin‐3‐ones 1a‐f with azomethine ylides, generating by the decarboxylative route from isatin 2 and sarcosine 3 , in moderate to good yields. The regiochemistry of designed dispiroheterocyclic compounds 4a‐f was established by single crystal X‐ray structure and spectroscopic techniques.