Synthesis of 5-Aryl- and 5-Heteroaryl-7-carboxyl-8-hydroxyquinaldines through
Suzuki Cross-Coupling Reaction with Potassium Organotrifluoroborates

Faten Sliman; Didier Desmaële

doi:10.1055/s-0029-1218585

PAPER

Synthesis of 5-Aryl- and 5-Heteroaryl-7-carboxyl-8-hydroxyquinaldines through Suzuki Cross-Coupling Reaction with Potassium Organotrifluoroborates

Faten Sliman, Didier Desmaële*
Université Paris-Sud, Faculté de Pharmacie, UMR CNRS 8076, 5 Rue Jean-Baptiste Clément, 92296 Châtenay-Malabry, France
Fax: +33(1)46835752; e-Mail: didier.desmaele@u-psud.fr;

Abstract

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Abstract

A series of 5-aryl- and 5-heteroaryl-7-carboxyl-8-hydroxyquinaldines were prepared from 5-bromo-7-methoxycarbonyl-8-benzyloxyquinaldine based on the Suzuki cross-coupling reaction using potassium organotrifluoroborates. An efficient method of deprotection of the 8-hydroxy group using a microwave-assisted hydrogen transfer reaction is reported.

Key words

quinolines - cross-coupling - boron - palladium - arylations

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References

<A NAME="RT15509SS-1A">1a</A> Palacios MA. Wang Z. Montes VA. Zyryanov GV. Anzenbacher P. J. Am. Chem. Soc. 2008, 130: 10307

<A NAME="RT15509SS-1B">1b</A> Kappaun S. Sović T. Stelzer F. Pogantsch A. Zojer E. Slugovc C. Org. Biomol. Chem. 2006, 4: 1503

<A NAME="RT15509SS-1C">1c</A> Jotterand N. Pearce DA. Imperiali B. J. Org. Chem. 2001, 66: 3224

<A NAME="RT15509SS-1D">1d</A> Chen CH. Shi J. Coord. Chem. Rev. 1998, 171: 161

<A NAME="RT15509SS-2A">2a</A> Ye Z. Fu Z. Zhong S. Xie F. Zhou X. Liu F. Yin D. J. Catal. 2009, 261: 110

<A NAME="RT15509SS-2B">2b</A> Kumbasar RA. Miner. Eng. 2009, 22 : 530

<A NAME="RT15509SS-2C">2c</A> Deraeve C. Maraval A. Vendier L. Faugeroux V. Pitié M. Meunier B. Eur. J. Inorg. Chem. 2008, 5622

<A NAME="RT15509SS-2D">2d</A> Izquierdo A. Compano R. Bars E. Talanta 1986, 33: 463

<A NAME="RT15509SS-3A">3a</A> Jin H. Cai RZ. Schacherer L. Jabri S. Tsiang M. Fardis M. Chen X. Chen JM. Kim CU. Bioorg. Med. Chem. Lett. 2006, 16: 3989

<A NAME="RT15509SS-3B">3b</A> Heinrich MR. Steglich W. Banwell MG. Kashman Y. Tetrahedon 2003, 59: 9239

<A NAME="RT15509SS-3C">3c</A> Shen A.-Y. Wu S.-N. Chiu C.-T. J. Pharm. Pharmacol. 1999, 51: 543

<A NAME="RT15509SS-3D">3d</A> Borchardt RT. J. Med. Chem. 1973, 16: 382

<A NAME="RT15509SS-4A">4a</A> Mekouar K. Mouscadet J.-F. Desmaële D. Subra F. Leh H. Savouré D. Auclair C. d’Angelo J. J. Med. Chem. 1998, 41: 2846

<A NAME="RT15509SS-4B">4b</A> Zouhiri F. Mouscadet J.-F. Mekouar K. Desmaële D. Savouré D. Leh H. Subra F. Le Bret M. Auclair C. d’Angelo J. J. Med. Chem. 2000, 43: 1533

<A NAME="RT15509SS-4C">4c</A> Polanski J. Zouhiri F. Jeanson L. Desmaële D. d’Angelo J. Mouscadet J.-F. Gieleciak R. Gasteiger J. Le Bret M. J. Med. Chem. 2002, 45: 4647

<A NAME="RT15509SS-4D">4d</A> Bénard C. Zouhiri F. Normand-Bayle M. Danet M. Desmaële D. Leh H. Mouscadet J.-F. Mbemba G. Thomas C.-M. Bonnenfant S. Le Bret M. d’Angelo J. Bioorg. Med. Chem. Lett. 2004, 14: 2473

<A NAME="RT15509SS-4E">4e</A> Courcot B. Firley D. Fraisse B. Becker P. Gillet J.-M. Pattison P. Chernyshov D. Sghaier M. Zouhiri F. Desmaële D. d’Angelo J. Bonhomme F. Geiger S. Ghermani NE. J. Phys. Chem. B 2007, 111: 6042

<A NAME="RT15509SS-5">5</A> Zouhiri F. Danet M. Bénard C. Normand-Bayle M. Mouscadet J.-F. Leh H. Thomas C.-M. Mbemba G. d’Angelo J. Desmaële D. Tetrahedron Lett. 2005, 46: 2201

<A NAME="RT15509SS-6">6</A> Miyaura N. Suzuki A. Chem. Rev. 1995, 95: 2457

<A NAME="RT15509SS-7A">7a</A> Pérez-Bolivar C. Montes VA. Anzenbacher P. Inorg. Chem. 2006, 45: 9610

<A NAME="RT15509SS-7B">7b</A> Montes VA. Pohl R. Shinar J. Anzenbacher P. Chem. Eur. J. 2006, 12: 4523

<A NAME="RT15509SS-7C">7c</A> Cui Y. Wang S. J. Org. Chem. 2006, 71: 6485

<A NAME="RT15509SS-7D">7d</A> Tsvetkov AV. Latyshev GV. Lukashev NV. Beletskaya IP. Tetrahedron Lett. 2002, 43: 7267

<A NAME="RT15509SS-7E">7e</A> Nakano Y. Imai D. Synthesis 1997, 1425

<A NAME="RT15509SS-8">8</A> Trécourt F. Mongin F. Mallet M. Quéguiner G. J. Heterocycl. Chem. 1995, 32: 1261

<A NAME="RT15509SS-9">9</A> Meek WH. Fuschman CHJ. J. Chem. Eng. Data 1969, 14: 388

<A NAME="RT15509SS-10">10</A> Guo W. Li J. Fan N. Wu W. Zhou P. Xia C. Synth. Commun. 2005, 35: 145

<A NAME="RT15509SS-11">11</A> Gooßen LJ. Rodriguez N. Gooßen K. Angew. Chem. Int. Ed. 2008, 47: 3100

<A NAME="RT15509SS-12A">12a</A> Darses S. Genêt J.-P. Brayer J.-L. Demoute J.-P. Tetrahedron Lett. 1997, 38: 4393

<A NAME="RT15509SS-12B">12b</A> Darses S. Genêt J.-P. Eur. J. Org. Chem. 2003, 4313

<A NAME="RT15509SS-13A">13a</A> Molander GA. Biollato B. J. Org. Chem. 2003, 68: 4302

<A NAME="RT15509SS-13B">13b</A> Molander GA. Canturk B. Kennedy LE. J. Org. Chem. 2009, 74: 973

<A NAME="RT15509SS-14">14</A> Reetz MT. Breinbauer R. Wanninger K. Tetrahedron Lett. 1996, 37: 4499

<A NAME="RT15509SS-15">15</A> Handy ST. Bregman H. Lewis J. Zhang X. Zhang Y. Tetrahedron Lett. 2003, 44: 427

<A NAME="RT15509SS-16">16</A> Felix AM. Heimer EP. Lambros TJ. Tzougraki C. Meienhofer J. J. Org. Chem. 1978, 43: 4194

<A NAME="RT15509SS-17">17</A> Quinn JF. Razzano DA. Golden KC. Gregg BT. Tetrahedron Lett. 2008, 49: 6137

<A NAME="RT15509SS-18">18</A> Hayashi T. Konishi M. Kobori Y. Kumada M. Higuchi T. Hirotsu K. J. Am. Chem. Soc. 1984, 106: 158

<A NAME="RT15509SS-19">19</A> Vedejs E. Chapman RW. Fields SC. Lin S. Schrimpf MR. J. Org. Chem. 1995, 60: 3020