133062-91-6Relevant articles and documents
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
Pritchard, Kaylene M.,Al-Rawi, Jasim
, p. 4076 - 4096 (2008)
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. Copyright Taylor & Francis Group, LLC.
