Sulfanyl radical mediated cyclization of aminyl radicals

被引：14
|
作者：
Montevecchi, PC [1 ]
Navacchia, ML [1 ]
机构：
[1] Univ Bologna, Dipartimento Chim Organ A Mangini, I-40136 Bologna, Italy
来源：
TETRAHEDRON LETTERS | 1998年 / 39卷 / 49期
关键词：
radicals and radical reactions; cyclisation; alkynes; amines;
D O I：
10.1016/S0040-4039(98)01998-4
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
1-(2-Aminophenyl)pent-1-yne 1 reacted with benzenethiol at 150 OC under radical conditions to give the thiol/alkyne adduct 2, the benzothiophene 4 and the indole 5. Reaction of 1 with benzenesulfanyl radicals produced from diphenyl disulfide in the absence of hydrogen donors gave only the indole 5 in high yields. Formation of indole 5 was explained in terms of sulfanyl radical mediated aminyl radical cyclization onto the alkyne triple bond. (C) 1998 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码：9077 / 9080
页数：4
相关论文
共 50 条
  • [21] Aminyl radical spotted
    不详
    CHEMICAL & ENGINEERING NEWS, 2005, 83 (03) : 34 - 34
  • [22] Discovery of Hypoiodite-Mediated Aminyl Radical Cyclization Lacking a Nitrogen Radical-Stabilizing Group: Application to Synthesis of an Oxazaspiroketal-Containing Cephalostatin Analog
    Koag, Myong
    Lee, Seongmin
    ORGANIC LETTERS, 2011, 13 (18) : 4766 - 4769
  • [23] Redox and acidity properties of alkyl- and arylamine radical cations and the corresponding aminyl radicals
    Jonsson, M
    Wayner, DDM
    Lusztyk, J
    JOURNAL OF PHYSICAL CHEMISTRY, 1996, 100 (44): : 17539 - 17543
  • [24] Silyl Radical Generation from Silylboronic Pinacol Esters through Substitution with Aminyl Radicals
    Lan, Hongyan
    Huo, Xiangyu
    Jia, Yinggang
    Wang, Dingyi
    ORGANIC LETTERS, 2024, 26 (05) : 1011 - 1016
  • [25] Alkyl Radical Generation from Alkylboronic Pinacol Esters through Substitution with Aminyl Radicals
    Wang, Zhe
    Wierich, Nick
    Zhang, Jingjing
    Daniliuc, Constantin G.
    Studer, Armido
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2023, 145 (16) : 8770 - 8775
  • [26] Alkene difunctionalization via aminyl radicals
    Zhao, Chunyang
    Zhu, Dongsheng
    Fu, Junkai
    TRENDS IN CHEMISTRY, 2022, 4 (11): : 1056 - 1057
  • [27] Radicals as Chiral Catalysts for Asymmetric Radical Cyclization Reactions
    Zhao, Quan-Qing
    Gu, Min
    Chen, Jia-Rong
    CHINESE JOURNAL OF CHEMISTRY, 2024, 42 (19) : 2412 - 2416
  • [28] Quinazolinones/Benzothiadiazines as Amidyl/Aminyl Radical Precursors for Controlled Cascade Cyclization via Photocatalyzed PCET
    Reddy, Mandapati Bhargava
    Prasanth, Kesavan
    Neerathilingam, Nalladhambi
    Anandhan, Ramasamy
    ORGANIC LETTERS, 2022, : 8158 - 8163
  • [29] A formal synthesis of (+)-α-allokainic acid via sulfanyl radical addition-cyclization reaction
    Miyata, O
    Ozawa, Y
    Ninomiya, T
    Aoe, K
    Hiramatsu, H
    Naito, T
    HETEROCYCLES, 1997, 46 : 321 - 333
  • [30] THE GENERATION OF AMINYL RADICALS FROM SULFENAMIDES
    BECKWITH, ALJ
    MAXWELL, BJ
    TSANAKTSIDIS, J
    AUSTRALIAN JOURNAL OF CHEMISTRY, 1991, 44 (12) : 1809 - 1812
12345