Multisubstituted benzo[b]furans through a copper- and/or palladium-catalyzed assembly and functionalization process

被引：29
作者：
Arcadi, Antonio [1 ]
Blesi, Federico [1 ]
Cacchi, Sandro [2 ]
Fabrizi, Giancarlo [2 ]
Goggiamani, Antonella [2 ]
Marinelli, Fabio [1 ]
机构：
[1] Univ Aquila, Dipartimento Sci Fis & Chim, I-67010 Laquila, Italy
[2] Univ Rome, Dipartimento Chim & Tecnol Farm, I-00185 Rome, Italy
来源：
TETRAHEDRON | 2013年 / 69卷 / 07期
关键词：
Copper; Palladium; Cross-couplings; Benzo[b]furans; One-pot process; CROSS-COUPLING REACTIONS; ONE-POT SYNTHESIS; O-ALKYNYLPHENOLS; INTRAMOLECULAR CYCLIZATION; TERMINAL ALKYNES; ARYL IODIDES; PRIVILEGED STRUCTURES; RECEPTOR ANTAGONISTS; CARBOCYCLIC CARBENE; SEROTONIN; 5-HT1A;
D O I：
10.1016/j.tet.2012.12.058
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Full details as well as the study of the scope, limitations, and further elaboration of a straightforward approach to the synthesis of 2,5,7-trisubstituted benzo[b]furans from 2-bromo- and 2-chloro-6-iodo-4-substituted phenols through a consecutive copper- and/or palladium-catalyzed assembly and functionalization process is described. Functionalization at the C(7) position is carried out by Suzuki-Miyaura cross-coupling, alkynylation, alkenylation, and C-N bond forming reactions. A one-pot protocol for the synthesis of 2,5,7-trisubstituted benzo[b]furans is also reported. (C) 2012 Elsevier Ltd. All rights reserved.
引用
收藏
页码：1857 / 1871
页数：15
相关论文
共 113 条
[41]   Potent, selective, and orally bioavailable matrix metalloproteinase-13 inhibitors for the treatment of osteoarthritis [J].
Hu, YH ;
Xiang, JS ;
DiGrandi, MJ ;
Du, XM ;
Ipek, M ;
Laakso, LM ;
Li, JC ;
Li, W ;
Rush, TS ;
Schmid, J ;
Skotnicki, JS ;
Tam, S ;
Thomason, JR ;
Wang, Q ;
Levin, JI .
BIOORGANIC & MEDICINAL CHEMISTRY, 2005, 13 (24) :6629-6644
[42]   Rapid and efficient Pd-catalyzed sonogashira coupling of aryl chlorides [J].
Huang, He ;
Liu, Hong ;
Jiang, Hualiang ;
Chen, Kaixian .
JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (15) :6037-6040
[43]   Efficient synthesis of functionalized dibenzofurans by domino 'twofold Heck/6π-electrocyclization' reactions of 2,3-di- and 2,3,5-tribromobenzofuran [J].
Hussain, Munawar ;
Hung, Nguyen Thai ;
Langer, Peter .
TETRAHEDRON LETTERS, 2009, 50 (27) :3929-3932
[44]   New benzo[b]furans as electroluminescent materials for emitting blue light [J].
Hwu, AR ;
Chuang, KS ;
Chuang, SH ;
Tsay, SC .
ORGANIC LETTERS, 2005, 7 (08) :1545-1548
[45]   Domino synthesis of 2-arylbenzo[b]furans by copper(II)-catalyzed coupling of o-iodophenols and aryl acetylenes [J].
Jaseer, E. A. ;
Prasad, D. J. C. ;
Sekar, Govindasamy .
TETRAHEDRON, 2010, 66 (11) :2077-2082
[46]   CuI/4-Hydro-L-proline as a More Effective Catalytic System for Coupling of Aryl Bromides with N-Boc Hydrazine and Aqueous Ammonia [J].
Jiang, Liqin ;
Lu, Xu ;
Zhang, Hui ;
Jiang, Yongwen ;
Ma, Dawei .
JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (12) :4542-4546
[47]   Design and synthesis of novel benzofurans as a new class of antifungal agents targeting fungal N-myristoyltransferase.: Part 3 [J].
Kawasaki, K ;
Masubuchi, M ;
Morikami, K ;
Sogabe, S ;
Aoyama, T ;
Ebiike, H ;
Niizuma, S ;
Hayase, M ;
Fujii, T ;
Sakata, K ;
Shindoh, H ;
Shiratori, Y ;
Aoki, Y ;
Ohtsuka, T ;
Shimma, N .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2003, 13 (01) :87-91
[48]   Synthesis of arylpiperazines via palladium-catalysed aromatic amination reactions of bromoarenes with N-tert-butoxycarbonylpiperazine [J].
Kerrigan, F ;
Martin, C ;
Thomas, GH .
TETRAHEDRON LETTERS, 1998, 39 (15) :2219-2222
[49]   A new structural alternative in benzo[b]furans for antimicrobial activity [J].
Khan, MW ;
Alam, MJ ;
Rashid, MA ;
Chowdhury, R .
BIOORGANIC & MEDICINAL CHEMISTRY, 2005, 13 (16) :4796-4805
[50]   New synthetic method for benzofurans from 2-(cyanomethyl)phenyl derivatives [J].
Kim, Hee Jun ;
Seo, Jai Woong ;
Lee, Min Hyung ;
Shin, Dong Seok ;
Kim, Hyeong Baik ;
Cho, Hyeongjin ;
Lee, Byoung Se ;
Chi, Dae Yoon .
TETRAHEDRON, 2012, 68 (21) :3942-3947
12345678910