Sonogashira Reactions with Propyne: Facile Synthesis of 4-Hydroxy-2-methylbenzofurans from Iodoresorcinols

被引：21

作者：

Berliner, Martin A. ^{[1
]}

Cordi, Eric M. ^{[2
]}

Dunetz, Joshua R. ^{[1
]}

Price, Kristin E. ^{[2
]}

机构：

[1] Pfizer Global Res & Dev, Res API, Pharmaceut Sci, Groton, CT 06340 USA

[2] Pfizer Global Res & Dev, Technol API, Pharmaceut Sci, Groton, CT 06340 USA

来源：

ORGANIC PROCESS RESEARCH & DEVELOPMENT | 2010年 / 14卷 / 01期

关键词：

CATALYZED SYNTHESIS; DERIVATIVES; SUZUKI; VERSATILE; ANALOGS; OLEFINS;

D O I：

10.1021/op900263b

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

The Sonogashira reaction of terminal alkynes and ortho-halophenols with subsequent cyclization is a well-precedented method for the synthesis of substituted benzofurans. Here we describe the extension of this method to the coupling of 2-iodoresorcinols and terminal alkynes, including propyne, to give 4-hydroxy-2-substituted benzofurans. In particular, we describe the screening, method development, and scaleup of the reaction with propyne using standard hydrogenation equipment.

引用

页码：180 / 187

页数：8

共 39 条

[11] INDIUM-CATALYZED CYCLOISOMERIZATION: PREPARATION OF 4-METHYLPYRROLO[1,2-a] QUINOLINE [J].

Fuerstner, Alois ;

Mamane, Victor ;

Seidel, Guenter ;

Laurich, Daniel .

ORGANIC SYNTHESES, 2006, 83 :103-+

[12]

Furstner A, 1998, SYNLETT, P161

[13] The versatile role of norbornene in C-H functionalization processes: concise synthesis of tetracyclic fused pyrroles via a threefold domino reaction [J].

Gericke, Kersten M. ;

Chai, David I. ;

Lautens, Mark .

TETRAHEDRON, 2008, 64 (26) :6002-6014

[14] Sonogashira/N-acyliminium ion aromatic π-cyclisation processes:: access to tetra- and pentacyclic lactams [J].

Grigg, Ronald ;

Sridharan, Visuvanathar ;

Sykes, David A. .

TETRAHEDRON, 2008, 64 (37) :8952-8962

[15] Dual bioactivity of resveratrol fatty alcohols: Differentiation of neural stem cells and modulation of neuroinflammation [J].

Hauss, Frederique ;

Liu, Jiawei ;

Michelucci, Alessandro ;

Coowar, Djalil ;

Morga, Eleonora ;

Heuschling, Paul ;

Luu, Bang .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2007, 17 (15) :4218-4222

[16] Liquid crystals from C3-symmetric mesogens for second-order nonlinear optics [J].

Hennrich, Gunther ;

Omenat, Ana ;

Asselberghs, Inge ;

Foerier, Stijn ;

Clays, Koen ;

Verbiest, Thierry ;

Serrano, Jose Luis .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (25) :4203-4206

[17]

HONG Y, 2005, Patent No. 0137395

[18] Utilization of Sequential Palladium-Catalyzed Cross-Coupling Reactions in the Stereospecific Synthesis of Trisubstituted Olefins [J].

Houpis, Ioannis N. ;

Shilds, Didier ;

Nettekoven, Ulrike ;

Schnyder, Anita ;

Bappert, Erhart ;

Weerts, Koen ;

Canters, Martine ;

Vermuelen, Wim .

ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2009, 13 (03) :598-606

[19] 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

[20] Highly diastereoselective approach toward (±)-tetraponerine T6 and analogues via the double cycloisomerization-reduction of bis-alkynylpyrimidines [J].

Kim, JT ;

Butt, J ;

Gevorgyan, V .

JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (17) :5638-5645

← 1 2 3 4 →