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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 38, 2008 - Issue 23
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Original Articles

Reaction of Ph3P(SCN)2 with Further Orthohydroxy Carboxylic Acid Systems, Including Substituted β-Keto Acids: Synthesis of Novel 2-Thio-1,3-oxazines and Their Subsequent Transformation with Amines

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Pages 4076-4096 | Received 21 Jan 2008, Published online: 31 Oct 2008
 

Abstract

We now report the first reaction of Ph3P(SCN)2 with 4,6-dihydroxy-5-methylisophthalic acid to give 10-methyl-2,8-dithio-1,3-oxazino-1,3-benzoxazine-4,6-dione. Also, the enol tautomer has been utilized in the reaction of β-keto acids with Ph3P(SCN)2 to give novel 2-thio-1,3-oxazines. Subsequent reaction of the 2-thio-1,3-oxazines with benzylamine resulted in opening of the oxazine ring and gave novel dibenzylamino-enamides, which could be cyclized to thiouracils. The reaction of 2-thio-1,3-oxazines with morpholine at low temperature led to the production of unstable 2-Mercapto-2-morpholino-1,3-oxazines. 2-Mercapto-2-morpholin-4-yl-2,3,5,6,7,8-hexahydro-4H-1,3-benzoxazin-4-one was observed to lose H2S at room temperature to give 2-morpholin-4-yl-5,6,7,8-tetrahydro-4H-1,3-benzoxazin-4-one, which was subsequently tested and found to exhibit some antiplatelet activity.

ACKNOWLEDGMENTS

The authors gratefully acknowledge the financial support of the Australian Research Council (Australian Postgraduate Award) and La Trobe University. They also acknowledge the preliminary work carried out by Jacob Nankervis.

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