Some chromeno[4,3-b]quinolines 4a-i were obtained from beta-chloro carboxyaldehydes 3a-c with different aniline derivatives namely, aniline, 4-fluoroaniline, and 2-aminophenol. Surprisingly, 3a-c reacted with 2-aminothiophenol and afforded the chromeno[3,4-c]quinoline derivatives 5a-c. Single-crystal X-ray diffraction studies of 4e and 5b provided good support for the established structure. Compounds 4b and 5b showed significant anti-inflammatory and ulcerogenic score activities compared to that of indomethacin.
Some new aldazino 4, pyrazolo 5, thieno 8, and thiooxopyrimidino chromenes 10 were prepared via reaction of the corresponding beta-chlorocarboxaldehyde 3 with hydrazine hydrate, mercaptoacetic acid, and thiourea, respectively. Wherever, 4-chlorochromene derivatives 2 along with 4-chlorochromen-3-carboxaldehyde derivatives 3 were prepared from the corresponding ketone 1 with Vilsmeier-Haack reagent. Some of the new products showed good anti-inflammatory, analgesic, anticonvulsant, and antiparkinsonian activities comparable to indomethacin, diclofenace, carbamazepine, and benztropine.
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