Electrophilic ipso-iodocyclization of N-(4-methylphenyl)propiolamides: selective synthesis of 8-methyleneazaspiro[4,5]trienes.
A novel and selective method for the synthesis of 8-methylenespiro[4,5]trienes via intramolecular electrophilic ipso-iodocyclization of N-(4-methylphenyl)propiolamides has been developed. In the presence of ICl or I 2, 8-methylene-1-azaspiro[4,5]trienes were selectively prepared from the electrophilic ipso-iodocyclization of N-(4-methylphenyl)propiolamides in moderate to good yields.
Yu
Quan-Fu
QF
Key Laboratory of Chemical Biology & Traditional Chinese Medicine Research (Ministry of Education), College of Chemistry and Chemical Engineering, Hunan Normal University, Changsha 410081, China.
Zhang
Yue-Hua
YH
Yin
Qin
Q
Tang
Bo-Xiao
BX
Tang
Ri-Yuan
RY
Zhong
Ping
P
Li
Jin-Heng
JH
D000577:Amides / Q000138:chemical synthesis* / Q000737:chemistry; D001372:Aza Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D003500:Cyclization; D004583:Electrons; D007455:Iodine / Q000737:chemistry*; D008745:Methylation; D015394:Molecular Structure; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry
D000577:Amides; D001372:Aza Compounds; D013141:Spiro Compounds; D007455:Iodine