ISSN:
0021-8383
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Substituted aromatic isothiocyanates with malonyl chloride yield 7-chloro-3-substituted-3,4-dihydro-4,5-dioxo-2-thio-2H,5H-pyrano [3,4-e]-1,3-oxazine (1).Alkyl isothiocyanates with malonyl chloride yield a mixture of 7-chloro-3-alkyl-2-thio pyranooxazine (2) and the 2-oxo-analogue (3).The pyrano oxazine 1 react stepwise with morpholine undergoing replacement of the 7-chloro substituent yielding the 7-morpholino analogue (4), then the pyrone ring was opened producing 5-morpholino carbonyl-4-oxo-3-substituted phenyl-2-thio-1,3-oxazine-6-ylacetomorpholid (5). Finally the oxazine ring was opened yielding 2-substituted phenyl carbomyl-3-morpholino-N,N-glutaconoyldimorpholine (6).Ethanol react with compound 1 at any molar ration causing the opening of the pyrone ring and retain the oxazine ring.Mass spectra. 1H-n.m.r., u.v. and i.r. spectroscopic data provided information about the fine structures of the products.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/prac.19883300603
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