- Synthesis of Substituted 1H-3,4-Dihydrodiazepinoindol-3-ones, 3,7-Dihydropyranoindol-7-ones and 6H-Oxazoloindoles
-
Ethyl 6-substituted 5-hydroxy-2-methylindole-3-carboxylates (1a,b), prepared by Nenitzescu reaction, Vilsmeier-Haack formylation using DMF and POCl3 form the corresponding 4-aldehydes (2a,b).These aldehydes undergo condensation with hydrazine hydrate (80percent) to produce 8-substituted 3,4-dihydro-7-hydroxy-2-methyldiazepinoindol-3-ones (3a,b).The reaction of 2a,b with acetic anhydride and triethylamine under reflux yields 5-substituted 1-carbethoxy-3,7-dihydro-2-methylpyranoindol-7-ones (4a,b).Ethyl 6-substituted 5-hydroxy-2-methyl-4-nitrosoindole-3-carboxylates (5a,b), prepared by nitrosation of 1a,b with acetic acid and sodium nitrite, when refluxed with benzylamine furnish the corresponding 4-substituted 6H-8-carbethoxy-7-methyl-2-phenyloxazoloindoles (6a,b).Following the above sequence of reactions ethyl 5-hydroxy-2-methylbenzindole-3-carboxylate has been converted into 1H-3,4-dihydro-7-hydroxy-2-methylbenzdiazepinoindol-3-one (9), 3-carbethoxy-1,6-dihydro-2-methylbenzpyranoindol-6-one (10) and 6H-4-carbethoxy-5-methyl-2-phenylbenzoxazoloindole (12).
- Hiremath, Shivayogi P.,Badami, Prema S.,Purohit, Muralidhar G.
-
p. 437 - 440
(2007/10/02)
-
- Synthesis of Substituted Diazepinoindol-4-ones
-
Various substituted ethyl 5-hydroxy-2-methylindole-3-carboxylates have been prepared by Nenitzescu reaction.These on condensation with hydrazine hydrate give the respective carboxyhydrazides, which react with formamide, acetic anhydride-acetic acid and be
- Hiremath, Shivayogi P.,Goudar, Naganagouda N.,Purohit, Muralidhar G.
-
p. 848 - 851
(2007/10/02)
-
- Synthesis of Substituted Oxadiazolylindoles
-
Indole-3-carboxyhydrazides (2a-d) are prepared and reacted with triethyl orthoformate to yield 3-(1',3',4'-oxadiazol-2'-yl)indoles (4a1-d1). 2a-d on reaction with benzaldehyde yield the corresponding schiff bases (3a-c).These on oxidative cyclodehydrogenation give 3-(5'-phenyl-1',3',4'-oxadiazol-2'-yl)indoles (4a2-d2). 2a-d also react with CS2 to produce 3-(5'-thione-1',3',4'-oxadiazol-2'-yl)indoles (5a-c) which undergo Mannich reaction with formaldehyde and 2-aminothiazoles to yield 7a-d.
- Hiremath, Shivayogi P.,Goudar, Naganagouda N.,Purohit, Muralidhar G.
-
p. 1031 - 1034
(2007/10/02)
-