Copper(I) Oxide Catalyzed N-Arylation of Azoles and Amines with Arylboronic Acid at Room Temperature under Base-Free Conditions

Bojja Sreedhar; Gopaladasu T. Venkanna; Kota Balaji Shiva Kumar; Vura Balasubrahmanyam

doi:10.1055/s-2008-1032184

PAPER

Copper(I) Oxide Catalyzed N-Arylation of Azoles and Amines with Arylboronic Acid at Room Temperature under Base-Free Conditions

Bojja Sreedhar*, Gopaladasu T. Venkanna, Kota Balaji Shiva Kumar, Vura Balasubrahmanyam
Inorganic and Physical Chemistry Division, Indian Institute of Chemical Technology, Hyderabad 500 007, India
Fax: +91(40)27160921; e-Mail: sreedharb@iict.res.in;

Abstract

Alle Artikel dieser Rubrik

Abstract

N-Arylation of azoles and amines with arylboronic acids was efficiently carried out with heterogeneous copper(I) oxide in methanol at room temperature under base-free conditions. The products N-arylazoles and N-arylamines were isolated in good to excellent yields. A variety of arylboronic acids and amines were converted to the corresponding N-arylazoles and N-arylamines, demonstrating the versatality of the reaction.

Key words

copper(I) oxide - N-arylimidazoles - N-arylamines - N-arylation - heterogeneous catalyst

Volltext

Referenzen

References

<A NAME="RP12007SS-1A">1a</A> Quan ML. Lam PYS. Han Q. Pinto DJP. He MY. Li R. Ellis CD. Clark CG. Teleha CA. Sun JH. Alexander RS. Bai S. Luettgen JM. Knabb RM. Wong PC. Wexler RR. J. Med. Chem. 2005, 48: 1729

<A NAME="RP12007SS-1B">1b</A> Dyck B. Goodfellow VS. Phillips T. Grey J. Haddach M. Rowbottom M. Naeve GS. Brown B. Saunders J. Bioorg. Med. Chem. Lett. 2004, 14: 1151

<A NAME="RP12007SS-1C">1c</A> Smallheer JM. Alexander RS. Wang J. Wang S. Nakajima S. Rossi KA. Smallwood A. Barbera F. Burdick D. Luettgen JM. Knabb RM. Wexler RR. Jadhav PK. Bioorg. Med. Chem. Lett. 2004, 14: 5263

<A NAME="RP12007SS-1D">1d</A> Venkatesan AM. Gu Y. Santos OD. Abe T. Agarwal A. Yang Y. Petersen PJ. Weiss WJ. Mansour TS. Nukaga M. Hujer AM. Bonomo RA. Knox JR. J. Med. Chem. 2004, 47: 6556

<A NAME="RP12007SS-1E">1e</A> Lange JHM. van Stuivenberg HH. Coolen HKAC. Adolfs TJP. McCreary AC. Keizer HG. Wals HC. Veerman W. Borst AJM. de Looff W. Verveer PC. Kruse CG. J. Med. Chem. 2005, 48: 1823

<A NAME="RP12007SS-1F">1f</A> Barchechath SD. Tawatao RI. Corr M. Carson DA. Cottam HB. J. Med. Chem. 2005, 48: 6409

<A NAME="RP12007SS-1G">1g</A> Mano T. Stevens RW. Kazuo A. Nakao YO. Sakakibara M. Okumura TT. Miyamoto K. Bioorg. Med. Chem. 2003, 11: 3879

<A NAME="RP12007SS-1H">1h</A> Mano T. Okumura Y. Sakakibara M. Okumura T. Tamura T. Miyamoto K. Stevens RW. J. Med. Chem. 2004, 47: 720

<A NAME="RP12007SS-1I">1i</A> Roppe J. Smith ND. Huang D. Tehrani L. Wang B. Anderson J. Brodkin J. Chung J. Jiang X. King C. Munoz B. Varney MA. Prasit P. Cosford NDP. J. Med. Chem. 2004, 47: 4645

<A NAME="RP12007SS-1J">1j</A> Voets M. Antes I. Scherer C. Muller-Viera U. Biemel K. Barassin C. Marchais-Oberwinkler S. Hartmann RW. J. Med. Chem. 2005, 48: 6632

<A NAME="RP12007SS-2A">2a</A> Iizuka K. Akahane K. Momose DI. Nakazawa M. Tanouchi T. Kawamura M. Ohyama I. Kajiwara I. Ignchi Y. Okada T. Taniguchi K. Miyamoto T. Hayashi M. J. Med. Chem. 1981, 24: 1139

<A NAME="RP12007SS-2B">2b</A> Cozzi P. Carganico G. Fusar D. Grossoni M. Menichincheri M. Pinciroli V. Tonani R. Vaghi F. Salvati P. J. Med. Chem. 1993, 36: 2964

<A NAME="RP12007SS-2C">2c</A> Wolfe J. Marcoux J.-F. Buchwald SL. Acc. Chem. Res. 1998, 31: 805

<A NAME="RP12007SS-2D">2d</A> Hartwig JF. Acc. Chem. Res. 1998, 31: 853

<A NAME="RP12007SS-3A">3a</A> Gungor T. Fouquet A. Teulon J.-M. Prevost D. Cazes M. Cloarec A. J. Med. Chem. 1992, 35: 4455

<A NAME="RP12007SS-3B">3b</A> Venuti MC. Stephenson RA. Alvarez R. Bruno JJ. Strosberg AM. J. Med. Chem. 1988, 31: 2136

<A NAME="RP12007SS-3C">3c</A> Ohmori J. Shimizu-Sasamata M. Okada M. Sakamoto SJ. J. Med. Chem. 1996, 39: 3971

<A NAME="RP12007SS-4A">4a</A> Martinez GR. Walker KAM. Hirshfeld DR. Bruno JJ. Yang DS. Maloney PJJ. J. Med. Chem. 1992, 35: 620

<A NAME="RP12007SS-4B">4b</A> Lo YS. Nolan JC. Maren TH. Welstead JR. Gripshover DF. Shamblee DA. J. Med. Chem. 1992, 35: 4790

<A NAME="RP12007SS-4C">4c</A> Pavik WJJW. Connors RE. Burns DS. Kurzweil EM. J. Med. Chem. 1993, 115: 7645

<A NAME="RP12007SS-5A">5a</A> Lam PYS. Deudon S. Averill KM. Li R. He MY. Deshong P. Clark CG. J. Am. Chem. Soc. 2000, 122: 7600

<A NAME="RP12007SS-5B">5b</A> Elliott GI. Konopelski JP. Org. Lett. 2000, 2: 3055

<A NAME="RP12007SS-5C">5c</A> Lopez-Alvarado P. Avendano C. Menendez JC. J. Org. Chem. 1996, 61: 5865

<A NAME="RP12007SS-5D">5d</A> Lopez-Alvarado P. Avendano C. Menendez JC. Tetrahedron Lett. 1992, 33: 659

<A NAME="RP12007SS-6A">6a</A> Lam PYS. Clark CG. Saubern S. Adams J. Winters MP. Chan DMT. Combs A. Tetrahedron Lett. 1998, 39: 2941

<A NAME="RP12007SS-6B">6b</A> Combs AP. Saubern S. Rafalski M. Lam PYS. Tetrahedron Lett. 1999, 40: 1623

<A NAME="RP12007SS-6C">6c</A> Lam PYS. Clark CG. Saubern S. Adams J. Averill KM. Chan DMT. Combs A. Synlett 2000, 674

<A NAME="RP12007SS-7A">7a</A> Collman JP. Zhong M. Zeng L. Costanzo S. J. Org. Chem. 2001, 66: 1528

<A NAME="RP12007SS-7B">7b</A> Collman JP. Zhong M. Org. Lett. 2000, 2: 1233

<A NAME="RP12007SS-8">8</A> Lan J.-B. Chen L. Yu X.-Q. You J.-S. Xie R.-G. Chem. Commun. 2004, 188

<A NAME="RP12007SS-9">9</A> van Berkel SS. van den Hoogenband A. Terpstra JW. Tromp M. van Leeuwen PWNM. van Strijdonck GPF. Tetrahedron Lett. 2004, 45: 7659

<A NAME="RP12007SS-10A">10a</A> Choudary BM. Sridhar Ch. Kantam ML. Venkanna GT. Sreedhar B. J. Am. Chem. Soc. 2005, 127: 9948

<A NAME="RP12007SS-10B">10b</A> Kantam ML. Venkanna GT. Sridhar Ch. Shiva Kumar KB. Tetrahedron Lett. 2006, 47: 3897

<A NAME="RP12007SS-10C">10c</A> Kantam ML. Venkanna GT. Sridhar C. Sreedhar B. Choudary BM. J. Org. Chem. 2006, 71: 9522