75996-85-9

Upstream product

• 57949-80-1 (3-carboxy-1-methylindol-2-yl)acetic acid anhydride 
• 64-17-5 ethanol 
• 57949-76-5 3-carboxy-1-methyl-1H-indole-2-acetic acid 
• 75996-84-8 methyl 2-(2-methoxy-2-oxoethyl)-1-methyl-1H-indole-3-carboxylate 
• 76013-18-8 3-(Methyl-phenyl-hydrazono)-pentanedioic acid dimethyl ester 

Downstream Products

• 75996-93-9 3-p-chlorophenylsulphonylamino-2-(2-hydroxyethyl)-1-methylindole 
• 75996-90-6 1-(4-Methoxy-phenyl)-5-methyl-1,3,4,5-tetrahydro-pyrano[4,3-b]indole 
• 75996-89-3 1,3,4,5-tetrahydro-5-methyl-1-phenylpyrano<4,3-b>indole 
• 111609-02-0 3,9-dihydro-9-methyl-3-<((4-nitrophenyl)methylene)amino>2H-pyrido<4,3-b>indol-2-one 

Relevant academic research and scientific papers

A Reinvestigation of the Synthesis of 3H-Diazepinoindoles. The synthesis of Pyridoindoles

Recently reported syntheses of 6-methyl-1,2,4,5-tetrahydro-1,4-dioxo-3Hdiazepinoindole (5) and 4-hydroxy-6-methyl-3Hdiazepinoindole (12) were reinvestigated and shown to be in error.The correct assignments for these respective structures are 3-amino-1,9-dihydro-9-methyl-2H-pyridoindol-2,4(3H)-dione (6) and 3-amino-3,9-dihydro-9-methyl-2H-pyridoindol-2-one (13).Condensation of 6 and 13 with p-nitrobenzaldehyde produced benzylidene derivatives, which confirmed the presence of the amino groups.

Synthesis of 3HDiazepinoindole and 3HDiazepinoindole Derivatives

The synthesis of two new derivatives of 3Hdiazepinoindole, 5 and 11, and one new derivative of 3Hdiazepinoindole, 16, are described.Compound 5 was obtained by the reaction of methyl 2-(3-methoxycarbonyl-1-methylindole)acetate 2, with hydrazine.Compound 11 was obtained in two ways from ethyl 2-(1-methylindole)acetate (8) by formylation and reaction with hydrazine.Compound 16 was obtained treating 3-(2-ethoxycarbonylindole)acetonitrile (14) with hydrazine.

Reactions of 4,5-Dihydro-5-methylpyranoindole-1,3-dione; a Synthesis of N-Methylisotryptophol

Boiling 4,5-dihydro-5-methylpyranoindole-1,3-dione (7) with alcohols followed by decarboxylation of the half-esters so formed leads to esters of 1-methylindol-2-ylacetic acid; reduction of these esters then affords N-methylisotryptophol (10).Reaction of 3-carboxy-1-methylindol-2-ylacetic acid (6; R=H) with acetic acid-sodium acetate gives 3,5-dimethylpyranoindol-1(5H)-one (17); with dimethylformamide-phosphorus oxychloride, 4-(NN-dimethylaminomethylene)-4,5-dihydro-5-methylpyranoindole-1,3-dione (22) was obtained.