Abstract
Chloro-6-ethyl-3-nitropyrano(3,2-c)quinoline-2,5(6H)-dione (3) was obtained by nitration followed by chlorination of 4-hydroxypyranoquinoline-2,5-dione 1. Substitution reactions of compound 3 with various nucleophiles, namely: sodium azide, amines, thiophenol and malono- nitrile, led to a series of novel 4-sustituted-3-nitropyranoquinolinones. Also, nucleophilic reactions of compound 3 with hydrazine, cyanoguanidine and S-methylisothiourea, involving ring opening-ring closure of the pyranoquinolinedione nucleus, are described.
Highlights
Pyrano[3,2-c]quinolinones are known as good synthons for many biologically important substituted quinolinones
Many quinolinone derivatives have been found active as antimalarial parasite agents,[5] antiamebics, and antischistosomal agents,[6,7,8] and to have antibacterial,[9,10] antiproliferative and antitubulin,[11] anti-hepatitis B virus (HBV)[12,13] anti-HIV-114 activities
Pyrano[3,2-c]quinolinones are able to undergo ring opening at C-2 and ring reclosure at C-4 when reacted with binucleophiles.[15,16]
Summary
Nucleophilic substitution and ring transformation reactions with 4-chloro-6-ethyl-3-nitropyrano[3,2-c]quinoline-2,5(6H)-dione. Abstract 4-Chloro-6-ethyl-3-nitropyrano[3,2-c]quinoline-2,5(6H)-dione (3) was obtained by nitration followed by chlorination of 4-hydroxypyranoquinoline-2,5-dione 1. Substitution reactions of compound 3 with various nucleophiles, namely: sodium azide, amines, thiophenol and malononitrile, led to a series of novel 4-sustituted-3-nitropyranoquinolinones. Nucleophilic reactions of compound 3 with hydrazine, cyanoguanidine and S-methylisothiourea, involving ring opening-ring closure of the pyranoquinolinedione nucleus, are described
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