Synthesis of Novel Spiro Pyrano[2, 3‐d]thiazolo[3, 2‐a]pyrimidine via 1, 3‐Dipolar Cycloaddition of Azomethine Ylide. (23rd July 2013)

• Record Type: Journal Article
• Authors: Ling, Yulin; Liu, Haochong; Zheng, Aiting; Li, Guobin; Li, Xiaofang
• Is Part Of: Journal of heterocyclic chemistry. Volume 50:Number 5(2013:Sep.)
• Page Start: 1009
• Page End: 1013
• Publication Date: 2013-07-23
• Subjects: Heterocyclic compounds -- Periodicals; 547.59
• DOI: 10.1002/jhet.740
• Languages: English
• ISSNs: 0022-152X

Abstract

<abstract abstract-type="main" xml:lang="en" id="jhet740-abs-0001"> <title> <x xml:space="preserve">Abstract</x> </title> <p id="jhet740-para-0002">The reaction involving 4‐phenyl‐octahydro‐pyrano[2, 3‐<italic>d</italic>]pyrimidine‐2‐thione, ethyl chloroacetate and the appropriate aromatic aldehyde yielded 2‐arylmethylidene‐5‐phenyl‐5<italic>a</italic>, 7, 8, 9<italic>a</italic>‐tetrahydro‐5<italic>H</italic>, 6<italic>H</italic>‐pyrano[2, 3‐<italic>d</italic>][1, 3]thiazolo[3, 2‐<italic>a</italic>]pyrimidin‐3(2<italic>H</italic>)‐ones. The <named-content id="d225e611" content-type="reactionType" xlink:type="simple" xmlns:xlink="http://www.w3.org/1999/xlink">1, 3‐dipolar cycloaddition</named-content> of 2‐arylmethylidene‐5‐phenyl‐5<italic>a</italic>, 7, 8, 9<italic>a</italic>‐tetrahydro‐5<italic>H</italic>, 6<italic>H</italic>‐pyrano[2, 3‐<italic>d</italic>][1, 3]thiazolo[3, 2‐<italic>a</italic>]pyrimidin‐3(2<italic>H</italic>)‐ones with azomethine ylide generated by a decarboxylative route from sarcosine and acenaphthenequinone afforded 4′‐aryl‐1′‐methyl‐5″‐phenyl‐5<italic>a</italic>″, 7″, 8″, 9<italic>a</italic>″‐tetrahydro‐2<italic>H</italic>, 5″<italic>H</italic>, 6″<italic>H</italic>‐dispiro[acenaphthylene‐1, 2′‐pyrrolidine‐3′, 2″‐pyrano[2, 3‐<italic>d</italic>][1, 3]thiazolo[3, 2‐<italic>a</italic>]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.</p> </abstract>