Harnessing the Polarizability of Conjugated Alkynes toward [2+2] Cycloaddition, Alkenylation, and Ring Expansion of Indoles

被引：26
作者：
Pradhan, Tapas R.
Kim, Hong Won
Park, Jin Kyoon [1 ,2 ]
机构：
[1] Pusan Natl Univ, Dept Chem, Busan 46241, South Korea
[2] Pusan Natl Univ, Chem Inst Funct Mat, Busan 46241, South Korea
来源：
ORGANIC LETTERS | 2018年 / 20卷 / 17期
关键词：
AXIALLY CHIRAL ALLENYLSILANES; HIGHLY SUBSTITUTED FURANS; ASYMMETRIC-SYNTHESIS; ENANTIOSELECTIVE SYNTHESIS; STEREOSELECTIVE-SYNTHESIS; DIMETHYL ACETYLENEDICARBOXYLATE; CYCLOISOMERIZATION REACTIONS; CATALYZED REACTIONS; ONE-POT; YNAMIDES;
D O I：
10.1021/acs.orglett.8b02230
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Reported is the utilization of electronically biased conjugated alkynes in the development of highly diastereo- and regioselective dearomative [2 + 2] cycloadditions, alkenylations, and ring expansions of electron-rich indoles. Regioselective protonations of cross- and linear-conjugated alkynes were found to be crucial for accessing various cyclobutene-fused indoline and alkenylated indole derivatives. Furthermore, the facile ring expansion of [2 + 2] keto adducts, which were successfully synthesized from ynones, provided 1H-benzo[b]azepine scaffolds.
引用
收藏
页码：5286 / 5290
页数：5
相关论文
共 69 条
[1]   Divergent C-H Annulation for Multifused N-Heterocycles: Regio- and Stereospecific Cyclizations of N-Alkynylindoles [J].
Alam, Khyarul ;
Hong, Sung Won ;
Oh, Kyung Hwan ;
Park, Jin Kyoon .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (43) :13387-13391
[2]  
Augusto J, 1983, J HETEROCYCLIC CHEM, V20, P1263
[3]   Au-Catalyzed Intermolecular [2+2] Cycloadditions between Chloroalkynes and Unactivated Alkenes [J].
Bai, Yu-Bin ;
Luo, Zaigang ;
Wang, Yuguang ;
Gao, Jin-Ming ;
Zhang, Liming .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2018, 140 (17) :5860-5865
[4]   Enantioselective One-Pot Organocatalytic Michael Addition/Gold-Catalyzed Tandem Acetalization/Cyclization [J].
Belot, Sebastien ;
Vogt, Kim A. ;
Besnard, Celine ;
Krause, Norbert ;
Alexakis, Alexandre .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (47) :8923-8926
[5]   Transition-Metal-Catalyzed Intramolecular Nucleophilic Addition of Carbonyl Groups to Alkynes [J].
Chen, Lianfen ;
Chen, Kai ;
Zhu, Shifa .
CHEM, 2018, 4 (06) :1208-1262
[6]   PHOTOCYCLOADDITION OF DIMETHYL ACETYLENEDICARBOXYLATE TO 1,3-DIMETHYLINDOLE [J].
DAVIS, PD ;
NECKERS, DC ;
BLOUNT, JR .
JOURNAL OF ORGANIC CHEMISTRY, 1980, 45 (03) :462-471
[7]   PHOTOCYCLOADDITION OF DIMETHYL ACETYLENEDICARBOXYLATE TO ACTIVATED INDOLES [J].
DAVIS, PD ;
NECKERS, DC .
JOURNAL OF ORGANIC CHEMISTRY, 1980, 45 (03) :456-462
[8]   Mild and Efficient C2-Alkenylation of Indoles with Alkynes Catalyzed by a Cobalt Complex [J].
Ding, Zhenhua ;
Yoshikai, Naohiko .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (19) :4698-4701
[9]   N-Substitution dependent stereoselectivity switch in palladium catalyzed hydroalkynylation of ynamides: a regio and stereoselective synthesis of ynenamides [J].
Dwivedi, Vikas ;
Babu, Madala Hari ;
Kant, Ruchir ;
Reddy, Maddi Sridhar .
CHEMICAL COMMUNICATIONS, 2015, 51 (81) :14996-14999
[10]   SYNTHESIS OF NEW TYPES OF TETRACYCLO[4.3.0.02,4.03,7]NONANE HYDROCARBONS BY CYCLOCODIMERIZATION OF NORBORNADIENE AND ITS DERIVATIVES WITH DIACETYLENES AND VINYLACETYLENES, CATALYZED BY LOW-VALENCE COBALT COMPLEXES [J].
DZHEMILEV, UM ;
KHUSNUTDINOV, RI ;
MUSLIMOV, ZS ;
TOLSTIKOV, GA .
BULLETIN OF THE ACADEMY OF SCIENCES OF THE USSR DIVISION OF CHEMICAL SCIENCE, 1987, 36 (05) :977-982
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