199604-39-2

Upstream product

• 18450-27-6 ethyl 3-formyl-1H-indole-2-carboxylate 
• 104-83-6 1-Chloro-4-(chloromethyl)benzene 
• 3770-50-1 2-carbethoxyindole 
• 109-77-3 malononitrile 
• 199604-37-0 1-(4-Chloro-benzyl)-3-formyl-1H-indole-2-carboxylic acid ethyl ester 

Downstream Products

• 199604-45-0 10-(4-Chloro-benzyl)-3-methoxy-1-oxo-1,2,5,10-tetrahydro-azepino[3,4-b]indole-4-carbonitrile 
• 199604-41-6 1-(4-Chloro-benzyl)-3-(2,2-dicyano-ethyl)-1H-indole-2-carboxylic acid ethyl ester 

Relevant academic research and scientific papers

Synthesis of Substituted 3-Amino-4-cyano-1-oxo-1,2,5,10-tetrahydroazepino[3,4-b]indoles

The preparation of 3-amino- and 3-dialkylamino-4-cyanoazepino[3,4-b]indoles bearing substituents on the aromatic nucleus and N10 is outlined. Starting from suitable substituted ethyl 3-formylindole-2-carboxylates 2, condensation with malononitrile (3) and subsequent sodium borohydride-reduction yielded ethyl 3-(2,2-dicyanoethyl)indole-2-carboxyIates 5 and 19, respectively, which were cyclized in boiling alkoxides to 3-alkoxy-4-cyanoazepino[3,4-b]indoles 10,11,20 and 21. This sequence constitutes a novel and flexible route to functional azepino[3,4-b]indoles. The aminolysis of 10,11,20 and 21 with different amines and ammonia yielded the title compounds which were screened for their possible biological activity.