Synthesis of 2-substituted benzo[b]thiophenes via gold(I)-NHC-catalyzed cyclization of 2-alkynyl thioanisoles

被引：14

作者：

Dillon, Christopher C. ^{[1
]}

Keophimphone, Bagieng ^{[1
]}

Sanchez, Melissa ^{[1
]}

Kaur, Parveen ^{[1
]}

Muchalski, Hubert ^{[1
]}

机构：

[1] Calif State Univ Fresno, 2555 E San Ramon Ave M-S SB70, Fresno, CA 93740 USA

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2018年 / 16卷 / 47期

关键词：

2,3-DISUBSTITUTED BENZOTHIOPHENES; ELECTROPHILIC CYCLIZATION; DERIVATIVES; ALKYNES; CARBOTHIOLATION; 5-LIPOXYGENASE; SERTACONAZOLE; ANNULATION; INHIBITORS; CATALYSIS;

D O I：

10.1039/c8ob02196a

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Benzo[b]thiophene heterocycles are important components of many important small molecule pharmaceuticals and drug candidates as well as organic semiconducting materials. Many methods have been developed for the construction of a benzo[b]thiophene core via cyclization reaction of alkynes. Although few catalytic reactions were disclosed, most methods rely on stoichiometric activation of alkynes. Here we report an efficient method for the synthesis of 2-substituted benzo[b]thiophenes from 2-alkynyl thioanisoles catalyzed by a gold(I)-IPr hydroxide that is applicable to a wide range of substrates with diverse electronic and steric properties. Additionally, we demonstrate experimentally that the acid additive and its conjugate base are essential to catalyst turnover.

引用

页码：9279 / 9284

页数：6

共 52 条

[1] Transition-Metal-Catalyzed Direct Arylation of (Hetero)Arenes by C-H Bond Cleavage [J].

Ackermann, Lutz ;

Vicente, Ruben ;

Kapdi, Anant R. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (52) :9792-9826

[2] Alternative synthetic methods through new developments in catalysis by gold [J].

Arcadi, Antonio .

CHEMICAL REVIEWS, 2008, 108 (08) :3266-3325

[3] Novel Benzo[b]thiophene Derivatives as New Potential Antidepressants with Rapid Onset of Action [J].

Berrade, Luis ;

Aisa, Barbara ;

Ramirez, Maria J. ;

Galiano, Silvia ;

Guccione, Salvatore ;

Moltzau, Lise Roman ;

Levy, Finn Olav ;

Nicoletti, Ferdinando ;

Battaglia, Giuseppe ;

Molinaro, Gemma ;

Aldana, Ignacio ;

Monge, Antonio ;

Perez-Silanes, Silvia .

JOURNAL OF MEDICINAL CHEMISTRY, 2011, 54 (08) :3086-3090

[4] Gold Catalysis 2.0 [J].

Braun, Ingo ;

Asiri, Abdullah Mohamed ;

Hashmi, A. Stephen K. .

ACS CATALYSIS, 2013, 3 (08) :1902-1907

[5] Photochromic crown-containing molecular switches of chemosensor activity [J].

Bren, Vladimir A. ;

Dubonosov, Alexander D. ;

Minkin, Vladimir I. ;

Tsukanov, Alexey V. ;

Gribanova, Tatyana N. ;

Shepelenko, Evgenii N. ;

Revinsky, Yurii V. ;

Rybalkin, Vladimir P. .

JOURNAL OF PHYSICAL ORGANIC CHEMISTRY, 2007, 20 (11) :917-928

[6] Gold-N-Heterocyclic Carbene Complexes of Mineral Acids [J].

Brill, Marcel ;

Nahra, Fady ;

Gomez-Herrera, Alberto ;

Zinser, Caroline ;

Cordes, David B. ;

Slawin, Alexandra M. Z. ;

Nolan, Steven P. .

CHEMCATCHEM, 2017, 9 (01) :117-120

[7]

CARTER GW, 1991, J PHARMACOL EXP THER, V256, P929

[8] Synthesis and evaluation of new arylbenzo[b]thiophene and diarylthiophene derivatives as inhibitors of the NorA multidrug transporter of Staphylococcus aureus [J].

Chabert, Jeremie Fournier dit ;

Marquez, Beatrice ;

Neville, Luc ;

Joucla, Lionel ;

Broussous, Sylvie ;

Bouhours, Pascale ;

David, Emilie ;

Pellet-Rostaing, Stephane ;

Marquet, Bernard ;

Moreau, Nicole ;

Lemaire, Marc .

BIOORGANIC & MEDICINAL CHEMISTRY, 2007, 15 (13) :4482-4497

[9] Gold(I)-Catalyzed Addition of Carboxylic Acids to Alkynes [J].

Chary, Bathoju Chandra ;

Kim, Sunggak .

JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (22) :7928-7931

[10] Synthesis of 2-substituted benzo[b]thiophene via a Pd-catalyzed coupling of 2-iodothiophenol with phenylacetylene [J].

Chen, Jingwen ;

Xiang, Haifeng ;

Yang, Li ;

Zhou, Xiangge .

RSC ADVANCES, 2017, 7 (13) :7753-7757

← 1 2 3 4 5 6 →