ISSN:
0021-8383
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
2-Arylidene-3,4-dihydro-1(2H)-naphthalenones 1 react with ethyl cyanoacetate in presence of ammonium acetate to give 4-aryl-7:8-benzo-3-cyano-1,2,3,4,5,6-hexahydro-2-oxoquinoline 2, 4-aryl-7:8-benzo-3-cyano-2-oxo-1,2,5,6-tetrahydroquinoline 3 and an oily product 4. Hydrolysis and decarboxylation of 4 gave β-aryl-β-(2-α-tetralonyl)propanoic acid 5. Thermolysis of 4 gave 2 and 3. Compounds 2 and 3 were also obtained by treatment of 1 with cyanoacetamide using piperidine as a catalyst. Condensation of 1 with diethyl malonate, cyclohexanone, and α-tetralone in presence of ammonium acetate afforded 4-aryl-7:8-benzo-1,2,3,4,5,6-hexahydro-2-oxoquinoline 8, 9-aryl-3:4-benzo-1,2,6,7,8,10-hexahydroacridine 9, and 9-aryl-3:4,5:6-dibenzo-1,2,7,8-tetrahydroacridine 10, respectively.
Additional Material:
1 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/prac.19753170405
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