A new, stereoselective, ring-forming reaction of 1,2-ethanedithiol with N-acylated indoles.
While attempting to prepare 2,5-dithiacyclopentyl derivatives from N-acyl 5-fluoroindole by reaction with 1,2-ethanedithiol we discovered that, instead of the expected product, annelation occurred to give a tricyclic compound containing a 3,6-dithiaazepine ring. This reaction is stereoselective and was found to be general for N-acylindoles, not being affected by substituents on the indole ring.
Tsotinis
Andrew
A
Faculty of Pharmacy, Department of Pharmaceutical Chemistry, University of Athens, Panepistimioupoli-Zografou, 157 71, Athens, Greece. tsotinis@pharm.uoa.gr
Eleutheriades
Andreas
A
Bari
Lorenzo Di
LD
Pescitelli
Gennaro
G
D003500:Cyclization; D007211:Indoles / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy / Q000379:methods / Q000592:standards; D008623:Mercaptoethanol / Q000031:analogs & derivatives* / Q000737:chemistry; D008958:Models, Molecular; D015394:Molecular Structure; D012015:Reference Standards; D013237:Stereoisomerism; D013438:Sulfhydryl Compounds / Q000138:chemical synthesis* / Q000737:chemistry
D007211:Indoles; D013438:Sulfhydryl Compounds; D008623:Mercaptoethanol; C031854:1,2-ethanedithiol