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Synthesis of Novel Spiro Pyrano[2,3‐ d ]thiazolo[3,2‐ a ]pyrimidine via 1,3‐Dipolar Cycloaddition of Azomethine Ylide
Author(s) -
Ling Yulin,
Liu Haochong,
Zheng Aiting,
Li Guobin,
Li Xiaofang
Publication year - 2013
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.740
Subject(s) - chemistry , sarcosine , azomethine ylide , cycloaddition , pyrrolidine , pyrimidine , 1,3 dipolar cycloaddition , isatin , medicinal chemistry , ylide , aldehyde , stereochemistry , organic chemistry , catalysis , glycine , biochemistry , amino acid
The reaction involving 4‐phenyl‐octahydro‐pyrano[2,3‐ d ]pyrimidine‐2‐thione, ethyl chloroacetate and the appropriate aromatic aldehyde yielded 2‐arylmethylidene‐5‐phenyl‐5 a ,7,8,9 a ‐tetrahydro‐5 H ,6 H ‐pyrano[2,3‐ d ][1,3]thiazolo[3,2‐ a ]pyrimidin‐3(2 H )‐ones. The 1,3‐dipolar cycloaddition of 2‐arylmethylidene‐5‐phenyl‐5 a ,7,8,9 a ‐tetrahydro‐5 H ,6 H ‐pyrano[2,3‐ d ][1,3]thiazolo[3,2‐ a ]pyrimidin‐3(2 H )‐ones with azomethine ylide generated by a decarboxylative route from sarcosine and acenaphthenequinone afforded 4′‐aryl‐1′‐methyl‐5″‐phenyl‐5 a ″,7″,8″,9 a ″‐tetrahydro‐2 H ,5″ H ,6″ H ‐dispiro[acenaphthylene‐1,2′‐pyrrolidine‐3′,2″‐pyrano[2,3‐ d ][1,3]thiazolo[3,2‐ a ]pyrimidine]‐2,3″‐diones in moderate yields. The structures of the products were determined and characterized thoroughly by NMR, MS, IR, elemental analysis, and X‐ray crystallographic analysis.