ISSN:
0170-2041
Keywords:
Thiophenes
;
Thieno[2,3-d]pyrimidines
;
Furans
;
Furo[2,3-d]pyrimidines
;
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
The reactions of 2-benzamido-4,5-dihydro-3-thiophene(-3-furan-)carbonitriles 1a-c (and 11a-c) with acetic (or propionic) anhydride in the presence of tin(IV) chloride give the corresponding 3-acetyl-5,6-dihydro-2-phenylthieno(-furo-)-[2,3-d]pyrimidin-4(3H)-ones 2a-c (and 12a-c) or 5,6-dihydro-2-phenyl-3-propionylthieno(-furo-)[2,3-d]pyrimidin-4(3H)-ones 3a-c (and 13a-c). Hydrolysis of compounds 2a-c (and 12a-c) or 3a-c (and 13a-c) leads to the corresponding N-acetyl-2-benzamido-4,5-dihydro-3-thiophene-(-3-furan-)carboxamides 4a-c (and 14a-c) or 2-benzamido-4,5-dihydro-N-propionyl-3-thiophene-(-3-furan-)carboxamides 5a-c (and 15a-c). The reaction of compounds 4a, b (or 14a, b) with acid anhydrides in the presence of potassium carbonate or triethylamine gives the corresponding 3-acyl-2-benzamido-4,5-dihydrothiophenes (or furans) 9, 10, 16, and 17.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/jlac.199419941007
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