132515-49-2

Upstream product

• 46397-90-4 N-[(1H-indol-3-yl)methyl]-N-ethylethanamine 
• 55-21-0 benzamide 
• 22259-53-6 3-aminomethylindole 
• 98-88-4 benzoyl chloride 
• 68769-69-7 2-((1H-indol-3-yl)methyl)isoindoline-1,3-dione 

Downstream Products

• 866836-59-1 3-(thiobenzoylaminomethyl)indole 
• 1597410-01-9 (4aS,9aS)-4a-chloro-2-phenyl-9-tosyl-4,4a,9,9a-tetrahydro-[1,3]oxazino[6,5-b]indole 
• 102664-68-6 1,3-bis-(benzoylamino-methyl)-indole 

Relevant academic research and scientific papers

Asymmetric chlorocyclization of indole-3-yl-benzamides for the construction of fused indolines

(DHQD)2PHAL catalyzed enantioselective chlorocyclization of indole-3-yl-benzamides was realized. Fused indolines containing a continuous quaternary carbon center and tertiary carbon center were obtained in good yields with excellent enantioselectivity (up to 98% yield and >99% ee).

Synthesis of thiazino[6,5-b]indole derivatives, analogues of the phytoalexin cyclobrassinin. A new method for preparation of 3-aminomethylindole

An efficient non-reductive synthesis of 3-aminomethylindole (6) was developed from gramine (1) via 3-phthalimidomethylindole (2). The reactions of amine 6 with substituted methyl dithiobenzoates gave 3- (arylthiocarbonylaminomethyl)indoles. The Hugerschoff ring-closure reactions of the thiobenzamide intermediates (11a-f) with phenyltrimethylammonium tribromide and subsequent basic treatment furnished 2-arylthiazino[6,5-b]indole derivatives (14a-f). By use of the latter bromine source, the phytoalexin cyclobrassinin (8) was prepared in a considerably higher yield than described previously. The structures of the novel products were elucidated by IR, 1H and 13C NMR spectroscopy, including 2D-HMQC, 2D-HMBC and DEPT measurements.