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

来源：

HETEROCYCLES | 2018年 / 97卷 / 02期

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

页码：719 / 728

页数：10

共 50 条

[41] One-pot synthesis of amides by aerobic oxidative coupling of alcohols or aldehydes with amines using supported gold and base as catalysts
Kegns, Soren
Mielby, Jerrik
Mentzel, Uffe V.
Jensen, Thomas
Fristrup, Peter
Riisager, Anders
CHEMICAL COMMUNICATIONS, 2012, 48 (18) : 2427 - 2429
[42] Platinum- and gold-catalyzed hydrative carbocyclization of oxo diynes for one-pot synthesis of benzopyrones and bicyclic spiro ketones
Das, Arindam
Chang, Hsu-Kai
Yang, Cheng-Hua
Liu, Rai-Shung
ORGANIC LETTERS, 2008, 10 (18) : 4061 - 4064
[43] Highly efficient one-pot synthesis of primary amides catalyzed by scandium(III) triflate under controlled MW
Allam, Bharat Kumar
Singh, Krishna Nand
TETRAHEDRON LETTERS, 2011, 52 (44) : 5851 - 5854
[44] Gold-catalyzed tandem cycloisomerization/Petasis-Ferrier rearrangement: a direct route to 3-alkoxyindanones from enynals and alcohols
Cao, Ziping
Zhang, Huaqing
Zhang, Xiaoxiang
Zhang, Ludan
Meng, Xin
Chen, Guang
Zhao, Xian-En
Sun, Xuejun
You, Jinmao
RSC ADVANCES, 2015, 5 (125) : 103155 - 103158
[45] Highly Efficient Heterogeneous Gold-catalyzed Direct Synthesis of Tertiary and Secondary Amines from Alcohols and Urea
He, Lin
Qian, Yue
Ding, Ran-Sheng
Liu, Yong-Mei
He, He-Yong
Fan, Kang-Nian
Cao, Yong
CHEMSUSCHEM, 2012, 5 (04) : 621 - 624
[46] VCL3 catalyzed efficient one-pot synthesis of a-amino phosphonates
Reddy, YT
Reddy, PN
Kumar, BS
Sreenivasulu, N
Rajitha, B
HETEROCYCLIC COMMUNICATIONS, 2005, 11 (02) : 153 - 156
[47] One-Pot Synthesis of Multi-Substituted 4-Pyrones by a Gold-Catalyzed Cascade of Wolff Rearrangement/[4+2] Cycloaddition/Elimination Reactions
Neupane, Pratik
Xia, Likai
Lee, Yong Rok
ADVANCED SYNTHESIS & CATALYSIS, 2014, 356 (11-12) : 2566 - 2574
[48] One-Pot Synthesis of 4-Heteroaryl-Substituted Pyrazoles: A Gold-Catalyzed Oxidation/1,2-Heteroaryl Migration Cascade Constitutes the Key Step
Yao, Xinbo
Wang, Tao
Zhang, Xi
Wang, Ping
Zhang, Bing
Wei, Junfa
Zhang, Zunting
ADVANCED SYNTHESIS & CATALYSIS, 2016, 358 (09) : 1534 - 1539
[49] Copper-catalyzed one-pot N-alkenylation and N-alkylation of amides: an efficient synthesis of substituted 2,3-dihydropyrroles
Zhou, Xiaobo
Zhang, Huimin
Yuan, Jiwei
Mai, Lugen
Li, Yanzhong
TETRAHEDRON LETTERS, 2007, 48 (40) : 7236 - 7239
[50] One-pot synthesis of highly substituted tetrahydrofurans from activated propargyl alcohols using Bu3P
Pedduri, Yakambram
Williamson, John S.
TETRAHEDRON LETTERS, 2008, 49 (41) : 6009 - 6012

← 1 2 3 4 5 →