Sonogashira coupling with aqueous ammonia directed to the synthesis of azotolane derivatives

被引：37

作者：

Ahmed, MSM ^{[1
]}

Mori, A ^{[1
]}

机构：

[1] Tokyo Inst Technol, Chem Resources Lab, Midori Ku, Yokohama, Kanagawa 2268503, Japan

来源：

TETRAHEDRON | 2004年 / 60卷 / 44期

关键词：

azotolane; aqueous ammonia; Sonogashira; palladium; terminal alkynes;

D O I：

10.1016/j.tet.2004.08.016

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Sonogashira coupling with aqueous ammonia is tolerable for the reaction of aryl iodides or terminal alkynes bearing an azobenzene group. The reaction of (4-heptyloxyphenyl)ethyne with (4-heptyloxyphenyl)-(4-iodophenyl)diazene in the presence of 1 mol% of PdCl2(PPh3)(2), 2 mol% of CuI, and 2 equiv of 0.5 M aqueous ammonia gives the corresponding azotolane in 87% isolated yield after stirring at room temperature for 15 h. (C) 2004 Elsevier Ltd. All rights reserved.

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收藏

页码：9977 / 9982

页数：6

相关论文

共 35 条

[1] Carbonylative Sonogashira coupling of terminal alkynes with aqueous ammonia [J].

Ahmed, MSM ;

Mori, A .

ORGANIC LETTERS, 2003, 5 (17) :3057-3060

[2] IPy2BF4-promoted intramolecular addition of masked and unmasked anilines to alkynes:: Direct assembly of 3-iodoindole cores [J].

Barluenga, J ;

Trincado, M ;

Rubio, E ;

González, JM .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (21) :2406-2409

[3] GAS-PHASE THERMAL REARRANGEMENTS OF POTENTIAL VINYLIDENE PRECURSORS TO SILYLBENZOFURANS AND SILYLBENZOPYRANS [J].

BARTON, TJ ;

GROH, BL .

JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (02) :158-166

[4] Peptide oligomers for holographic data storage [J].

Berg, RH ;

Hvilsted, S ;

Ramanujam, PS .

NATURE, 1996, 383 (6600) :505-508

[5] INDOLES BENZOFURANS PHTHALIDES AND TOLANES VIA COPPER(1) ACETYLIDES [J].

CASTRO, CE ;

GAUGHAN, EJ ;

OWSLEY, DC .

JOURNAL OF ORGANIC CHEMISTRY, 1966, 31 (12) :4071-+

[6] REVERSIBLE DIGITAL AND HOLOGRAPHIC OPTICAL STORAGE IN POLYMERIC LIQUID-CRYSTALS [J].

EICH, M ;

WENDORFF, JH ;

RECK, B ;

RINGSDORF, H .

MAKROMOLEKULARE CHEMIE-RAPID COMMUNICATIONS, 1987, 8 (01) :59-63

[7] Molecular construction based on icosahedral carboranes and aromatic N,N′-dimethylurea groups.: Aromatic layered molecules and a transition metal complex [J].

Endo, Y ;

Songkram, C ;

Yamasaki, R ;

Tanatani, A ;

Kagechika, H ;

Takaishi, K ;

Yamaguchi, K .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2002, 657 (1-2) :48-58

[8]

Hasegawa M, 1999, ADV MATER, V11, P675

[9] Photomodulation of liquid crystal orientations for photonic applications [J].

Ikeda, T .

JOURNAL OF MATERIALS CHEMISTRY, 2003, 13 (09) :2037-2057

[10] PREPARATION AND PROPERTIES OF POLYAMIDES AND POLYIMIDES CONTAINING BIBENZYL, STILBENE, AND TOLAN STRUCTURES [J].

INOUE, K ;

IMAI, Y .

JOURNAL OF POLYMER SCIENCE PART A-POLYMER CHEMISTRY, 1976, 14 (07) :1599-1607

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