EFFICIENT ONE-POT SYNTHESIS OF SUBSTITUTED OXAZOLES FROM 3-TRIMETHYLSILYLPROPARGYLIC ALCOHOLS AND AMIDES BY GOLD-CATALYZED SUBSTITUTION FOLLOWED BY CYCLOISOMERIZATION

被引:7
|
作者
Morita, Nobuyoshi [1 ]
Sano, Aoi [1 ]
Sone, Ayako [1 ]
Aonuma, Shino [1 ]
Matsunaga, Arisa [1 ]
Hashimoto, Yoshimitsu [1 ]
Tamura, Osamu [1 ]
机构
[1] Showa Pharmaceut Univ, Machida, Tokyo 1948543, Japan
关键词
PROPARGYLIC ALCOHOLS; GOLD(I)/(III)-CATALYZED SYNTHESIS; FUNCTIONALIZED OXAZOLES; MEDIATED SYNTHESIS; CYCLIZATION; SEQUENCE;
D O I
10.3987/COM-18-S(T)81
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
3-Trimethylsilylpropargylic alcohols 1, on treatment with amides 2 in the presence of catalytic amounts of cationic gold(III), underwent propargylic substitution followed by cycloisomerization, in which the key feature is the beta-cation-stabilizing effect of the silicon atom of 1.
引用
收藏
页码:719 / 728
页数:10
相关论文
共 50 条
  • [21] An Efficient One-Pot Synthesis of Nitriles from Alcohols or Aldehydes with NH3 Catalyzed by a Supported Ruthenium Hydroxide
    Takamichi Oishi
    Kazuya Yamaguchi
    Noritaka Mizuno
    Topics in Catalysis, 2010, 53 : 479 - 486
  • [22] Efficient one-pot synthesis of dendritic benzyl azides from their alcohols
    Lee, Jae Wook
    Han, Seung Choul
    Lee, Yong-gyun
    Kim, Ji Hyeon
    Oh, Jinho
    BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2008, 29 (05) : 1055 - 1058
  • [23] Gold(I)-Catalyzed Synthesis of 2,2′-Biindoles via One-Pot Double Cycloisomerization Strategy
    Ibarra-Gutierrez, Jaime G.
    Solorio-Alvarado, Cesar R.
    Chacon-Garcia, Luis
    Lopez, Jesus Adrian
    Delgado-Piedra, B. Yoaly
    Segura-Quezada, Luis A.
    Hernandez-Velazquez, Edson D.
    Garcia-Duenas, Ana K.
    JOURNAL OF ORGANIC CHEMISTRY, 2024, 89 (23): : 17069 - 17089
  • [24] One-pot synthesis of alcohols from olefins catalyzed by rhodium and ruthenium complexes
    Zakzeski, Joseph
    Lee, Hae Ryun
    Leung, Yi Ling
    Bell, Alexis T.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2010, 239
  • [25] One-pot synthesis of alcohols from olefins catalyzed by rhodium and ruthenium complexes
    Zakzeski, Joseph
    Lee, Hae Ryun
    Leung, Yi Ling
    Bell, Alexis T.
    APPLIED CATALYSIS A-GENERAL, 2010, 374 (1-2) : 201 - 212
  • [26] An efficient one-pot synthesis of highly substituted furans catalyzed by N-bromosuccinimide
    Ghasemnejad-Bosra, Hassan
    Faraje, Mohammad
    Habibzadeh, Setareh
    Ramzanian-Lehmali, Farhad
    JOURNAL OF THE SERBIAN CHEMICAL SOCIETY, 2010, 75 (03) : 299 - 305
  • [27] Ruthenium-catalyzed one-pot synthesis of primary amides from aldehydes in water
    Garcia-Alvarez, Rocio
    Diaz-Alvarez, Alba E.
    Crochet, Pascale
    Cadierno, Victorio
    RSC ADVANCES, 2013, 3 (17): : 5889 - 5894
  • [28] One-Pot Synthesis of Substituted Furans Using Cu(OTf)2-Catalyzed Propargylation/Cycloisomerization Tandem Reaction
    Pan, Ying-ming
    Zhao, Su-yan
    Ji, Wen-hua
    Zhan, Zhuang-ping
    JOURNAL OF COMBINATORIAL CHEMISTRY, 2009, 11 (01): : 103 - 109
  • [29] Ruthenium- and gold-catalysed sequential reactions: a straightforward synthesis of substituted oxazoles from propargylic alcohols and amides
    Milton, MD
    Inada, Y
    Nishibayashi, Y
    Uemura, S
    CHEMICAL COMMUNICATIONS, 2004, (23) : 2712 - 2713
  • [30] Cobalt(II) Phthalocyanine Catalyzed One-Pot Synthesis of 2-Substituted Benzimidazoles, Benzothiazoles and Benzoxazoles from Substituted Benzyl Alcohols
    Narang, Uma
    Yadav, Kumar Karitkey
    Bhattacharya, Soumee
    Chauhan, Shive M. S.
    CHEMISTRYSELECT, 2017, 2 (24): : 7135 - 7140