Synthesis of spirodienones by intramolecular ipso-cyclization of N-methoxy-(4-halogenophenyl)amides using [hydroxy(tosyloxy)iodo]benzene in trifluoroethanol.
Spirodienones bearing the 1-azaspiro[4.5]decane ring system have been synthesized from N-methoxy-(4-halogenophenyl)amides by the intramolecular ipso attack of a nitrenium ion generated with [hydroxy(tosyloxy)iodo]benzene in trifluoroethanol.
Miyazawa
Etsuko
E
Faculty of Pharmaceutical Sciences, Josai University, 1-1 Keyakidai, Sakado, Saitama 350-0295, Japan.
Sakamoto
Takeshi
T
Kikugawa
Yasuo
Y
D000470:Alkaloids / Q000737:chemistry; D000577:Amides / Q000737:chemistry; D001372:Aza Compounds / Q000737:chemistry; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D003500:Cyclization; D006846:Hydrocarbons, Halogenated / Q000737:chemistry*; D015394:Molecular Structure; D009943:Organophosphorus Compounds / Q000737:chemistry; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry
D000470:Alkaloids; D000577:Amides; D001372:Aza Compounds; C098358:FR 901483; D006846:Hydrocarbons, Halogenated; D009943:Organophosphorus Compounds; D013141:Spiro Compounds; C429313:TAN1251A; C431548:lepadiformine