2,3-disubstituted benzo[b]thiophenes from diarylalkynes via electrophilic addition-cyclization and palladium-catalyzed cross-coupling

被引：19

作者：

Lamanna, Giuseppe ^{[1
]}

Menichetti, Stefano ^{[1
]}

机构：

[1] Univ Florence, Lab Progettaz Sintesi & Studio Eterocicli Biol At, I-50019 Sesto Fiorentino, FI, Italy

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2007年 / 349卷 / 13期

关键词：

benzo[b]thiophenes; cross-coupling; electrophilic addition; electrophilic substitution; phthalimidesulfenyl chloride; solid phase synthesis; DIRECTED THROMBIN INHIBITORS; ONE-POT SYNTHESIS; ARYL; DERIVATIVES; ANTIESTROGENS; PRECATALYST; CHLORIDES; NHC;

D O I：

10.1002/adsc.200700172

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

Diarylalkynes are readily transformed in 3-chlorobenzo[b]thiophenes in a two-step electrophilic addition-cyclization procedure that runs highly efficiently in solution or in the solid phase. The heteroaromatic carbon-chlorine bond participates in palladium-catalyzed Suzuki-Miyaura or Buchwald-Hartwig cross-couplings to give, in a single step, 2,3-disubstituted derivatives of pharmacological relevance.

引用

页码：2188 / 2194

页数：7

共 48 条

[21] Facile synthesis and palladium-catalyzed cross-coupling reactions of 2,3-bis(pinacolatoboryl)-1,3-butadiene
Shimizu, Masaki
Kurahashi, Takuya
Shimono, Katsuhiro
Tanaka, Kei
Nagao, Ikuhiro
Kiyomoto, Shin-Ichi
Hiyama, Tamejiro
CHEMISTRY-AN ASIAN JOURNAL, 2007, 2 (11) : 1400 - 1408
[22] Regioselective synthesis of 2,3-disubstituted 1-alkyl pyrrolo[2,3-b] quinoxalines through palladium-catalyzed Heck reaction of chalcones and evaluation of their anti-bacterial activities
Besharati-Seidani, Tayebeh
Keivanloo, Ali
Kaboudin, Babak
Yoshida, Akihiro
Yokomatsu, Tsutomu
TETRAHEDRON, 2018, 74 (19) : 2350 - 2358
[23] Palladium-Catalyzed Cross-Coupling of 1,4-Disubstituted 5-Iodo-1,2,3-triazoles with Organotin Reagents
Carcenac, Yvan
David-Quillot, Franck
Abarbri, Mohamed
Duchene, Alain
Thibonnet, Jerome
SYNTHESIS-STUTTGART, 2013, 45 (05): : 633 - 638
[24] A Palladium-Catalyzed Domino Approach to 2,3-Disubstituted Benzofurans via an Intermolecular Carbopalladation/C(sp3)-H Functionalization/Isomerization Sequence
Boominathan, Siva Senthil Kumar
Hou, Ruei-Jhih
Hu, Wan-Ping
Huang, Po-Jui
Wang, Jeh-Jeng
ADVANCED SYNTHESIS & CATALYSIS, 2016, 358 (18) : 2984 - 2989
[25] Photochemical route for the synthesis of novel 2-monosubstituted pyrido[2,3-d]pyrimidines by palladium-catalyzed cross-coupling reactions
Yassine Riadi
Mohammed Geesi
Chemical Papers, 2018, 72 : 697 - 701
[26] The Recent Development of Phosphine Ligands Derived from 2-Phosphino-Substituted Heterocycles and Their Applications in Palladium-Catalyzed Cross-Coupling Reactions
Wong, Shun Man
So, Chau Ming
Kwong, Fuk Yee
SYNLETT, 2012, (08) : 1132 - 1153
[27] Highly efficient synthesis of 5,6-disubstituted-5H-pyrrolo[2,3-b]pyrazine-2,3-dicarbonitriles through a one-pot palladium-catalyzed coupling reaction/cyclization in water
Keivanloo, Ali
Bakherad, Mohammad
Nasr-Isfahani, Hossein
Esmaily, Somayeh
TETRAHEDRON LETTERS, 2012, 53 (25) : 3126 - 3130
[28] A general approach to selective functionalization of 1,2,4-triazines using organometallics in palladium-catalyzed cross-coupling and addition reactions
Alphonse, FA
Suzenet, F
Keromnes, A
Lebret, B
Guillaumet, G
SYNTHESIS-STUTTGART, 2004, (17): : 2893 - 2899
[29] Access to polysubstituted indoles or benzothiophenes via palladium-catalyzed cross-coupling of furfural tosylhydrazones with 2-iodoanilines or 2-iodothiophenols
Yin, Biaolin
Zhang, Xiaoyu
Zhang, Xiaoting
Peng, Hui
Zhou, Wen
Liu, Bo
Jiang, Huanfeng
CHEMICAL COMMUNICATIONS, 2015, 51 (28) : 6126 - 6129
[30] Synthesis of 2,3-Disubstituted 1,4-Naphthoquinones via Metal-Free C(sp2)-H Functionalization Followed by Suzuki Cross-Coupling Reactions
Borah, Ashwini
Sharma, Abhilash
Hazarika, Hemanta
Gogoi, Pranjal
CHEMISTRYSELECT, 2017, 2 (31): : 9999 - 10003

← 1 2 3 4 5 →