RADICAL CYCLIZATIONS OF N-VINYLIC ALPHA-CHLOROACETAMIDES - 5-ENDO-TRIG AND 4-EXO-TRIG CYCLIZATIONS

被引:98
|
作者
ISHIBASHI, H
NAKAMURA, N
SATO, T
TAKEUCHI, M
IKEDA, M
机构
[1] Kyoto Pharmaceutical University, Kyoto, 607, Misasagi, Yamashina
关键词
D O I
10.1016/S0040-4039(00)74314-0
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Bu3SnH mediated radical cyclizations of N-vinylic alpha-chloroacetamides proceeded in a "disfavored" 5-endo-trig manner to give five-membered lactams. Some exceptions where the 4-exo cyclization predominates are also described.
引用
收藏
页码:1725 / 1728
页数:4
相关论文
共 50 条
  • [21] Radical-mediated 5-Exo-Trig cyclizations of 3-silylhepta-1,6-dienes
    James, P
    Schenk, K
    Landais, Y
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (09): : 3630 - 3633
  • [22] Synthesis of bis(enolnonaflates) and their 4-exo-trig-cyclizations by intramolecular Heck reactions
    Bräse, S
    [J]. SYNLETT, 1999, (10) : 1654 - 1656
  • [23] ELECTRONIC VERSUS STERIC EFFECTS IN 5-ENDO-TRIG-LIKE ELECTROPHILIC CYCLIZATIONS
    LANDAIS, Y
    PLANCHENAULT, D
    [J]. SYNLETT, 1995, (11) : 1191 - &
  • [24] 6-ENDO-TRIG RADICAL CYCLIZATIONS - SYNTHETIC APPROACHES TO THE A-B-RING OF (+/-)-FORSKOLIN
    ANIES, C
    BILLOT, L
    LALLEMAND, JY
    PANCRAZI, A
    [J]. TETRAHEDRON LETTERS, 1995, 36 (40) : 7247 - 7250
  • [25] Recent advances of 5-endo-trig radical cyclization: promoting strategies and applications
    Zhou, Yulu
    Xu, Sangxuan
    Zhang, Xuemei
    Zhou, Lanxi
    Zheng, Hanliang
    Zhu, Gangguo
    [J]. CHEMICAL COMMUNICATIONS, 2024, 60 (74) : 10098 - 10111
  • [26] Synthesis of pterocarpans by means of a "disfavored" 5-endo-trig radical cyclization reaction
    Santhosh, KC
    Gopalsamy, A
    Balasubramanian, KK
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2001, 2001 (18) : 3461 - 3466
  • [27] Divergent chemical synthesis of prolines bearing fluorinated one-carbon units at the 4-position via nucleophilic 5-endo-trig cyclizations
    Nadano, Ryo
    Iwai, Yu
    Mori, Takashi
    Ichikawa, Junji
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (23): : 8748 - 8754
  • [28] Synthetic Strategies Directed Towards 5a-Carbahexopyranoses and Derivatives Based on 6-endo-trig Radical Cyclizations
    Gomez, Ana M.
    Uriel, Clara
    Company, Maria D.
    Cristobal Lopez, J.
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2011, 2011 (35) : 7116 - 7132
  • [29] Synthesis of aryl ring-fused benzimidazolequinones using 6-exo-trig radical cyclizations
    Moriarty, Eoin
    Aldabbagh, Fawaz
    [J]. TETRAHEDRON LETTERS, 2009, 50 (37) : 5251 - 5253
  • [30] Recent Advances on 5-endo-Trig Radical Cyclization of All-Carbon Systems
    Zheng Hanliang
    Su Jingwen
    Zhou Yulu
    Zhu Gangguo
    [J]. CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2022, 42 (12) : 4060 - 4066