Synthesis and Biological Activities of 1-Keto-3-Carboxy-6,7-Methylenedioxy-1,2,3,4-Tetrahydronaphthalene Derivatives

Abstract

1-Keto-3-carboxy - 6,7-methylenedioxy - 1,2,3,4-tetrahydronaphthalene
(I) was converted to its ester, 1-keto-3-carbmethoxy-6,7-methylenedioxy-
1,2,3,4-tetrahydronaphthalene (II) which was treated with hydrazine
hydrate to give 1-keto-3-hydrazocarbonyl-6,7-methylenedioxy-1,2,3,4-
tetrahydronaphthalene (III). Compound (III) was condensed with various
aromatic aldehydes to give corresponding 3-arylidene hydrazocarbonyl-
6,7-methylenedioxy- 1,2,3,4-tetrahydronaphthalene (IVa-h), On condensation
with various substituted benzoxazones, compound (III) gave
quinazoline-4-(3H)-one derivatives (Vi-k). Above condensation reactions
were also carried out in a microwave oven at 10% energy. Compound (I)
was treated with various benzhydrazides in presence of excess of POCI₃
to yield substituted oxadiazoles (VIa-b).