Direct synthesis of fused 1,2,3,4,5-pentathiepins.
Treatment of nucleophilic heterocycles like pyrroles and thiophenes, and their tetrahydro derivatives, with S2Cl2 and DABCO in chloroform at room temperature provides a simple one-pot synthesis of fused mono and bispentathiepins. N-Methylpyrrole and its 2-chloro and 2,5-dichloro derivatives and N-methylpyrrolidine all give the same dichloropentathiepin 1a. N-Ethyl, isopropyl and tert-butylpyrrolidine behave similarly; the isopropylpyrrolidine also gives the bispentathiepin 6which undergoes an intriguing rearrangement to the symmetrical monopentathiepin 1c. N-Methyl and ethyl indole give either 2,3-dichloro derivatives 8 or the pentathiepinoindoles 9, depending upon the reaction conditions. Thiophene and tetrahydrothiophene give the pentathiepin 10. X-Ray crystal structures are provided for the pentathiepins 1a and 1d, and possible reaction pathways are suggested for the extensive cascade reactions reported.
Amelichev
Stanislav A
SA
N. D. Zelinsky Institute of Organic Chemistry, Academy of Sciences, Leninsky Prospect, 47, 119991, Moscow, Russia.
Konstantinova
Lidia S
LS
Lyssenko
Konstantin A
KA
Rakitin
Oleg A
OA
Rees
Charles W
CW
D000935:Antifungal Agents / Q000494:pharmacology*; D002384:Catalysis; D002725:Chloroform / Q000737:chemistry; D018360:Crystallography, X-Ray; D015394:Molecular Structure; D011758:Pyrroles / Q000737:chemistry; D011759:Pyrrolidines / Q000737:chemistry; D013237:Stereoisomerism; D013696:Temperature; D013846:Thiepins / Q000138:chemical synthesis*; D013876:Thiophenes / Q000138:chemical synthesis*
D000935:Antifungal Agents; D011758:Pyrroles; D011759:Pyrrolidines; D013846:Thiepins; D013876:Thiophenes; D002725:Chloroform