Simple conversion of enamines to 2H-azirines and their rearrangements under thermal conditions.
A variety of substituted enamine derivatives were first found to be conveniently converted to the corresponding 2H-azirines mediated by phenyliodine (III) diacetate (PIDA). The formed 2-aryl-2H-azirines could be applied in the synthesis of indole-3-carbonitriles or isoxazoles via thermal rearrangements.
Tianjin Key Laboratory for Modern Drug Delivery & High-Efficiency, School of Pharmaceutical Science and Technology, Tianjin University, Tianjin 300072, China.
Xiaoxun
X
Li
Yunfei
Y
Du
Zhidan
Z
Liang
Xiangke
X
Li
Yan
Y
Pan
Kang
K
Zhao
D000588:Amines / Q000737:chemistry*; D001389:Azirines / Q000138:chemical synthesis* / Q000737:chemistry; D018360:Crystallography, X-Ray; D003500:Cyclization; D004055:Differential Thermal Analysis; D007211:Indoles / Q000138:chemical synthesis / Q000737:chemistry; D007555:Isoxazoles / Q000138:chemical synthesis / Q000737:chemistry; D015394:Molecular Structure; D009570:Nitriles / Q000138:chemical synthesis / Q000737:chemistry; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
D000588:Amines; D001389:Azirines; D007211:Indoles; D007555:Isoxazoles; D009570:Nitriles