Efficient Copper-Catalyzed
Synthesis of Fused Pyridoquinazolones

Lujun Chen; Hua Fu; Renzhong Qiao

doi:10.1055/s-0030-1260968

LETTER

Efficient Copper-Catalyzed Synthesis of Fused Pyridoquinazolones

Lujun Chen^a,b, Hua Fu*^a, Renzhong Qiao*^b
^a Key Laboratory of Bioorganic Phosphorus Chemistry and Chemical Biology (Ministry of Education), Department of Chemistry, Tsinghua University, Beijing 100084, P. R. of China
Fax: +86(10)62781695; e-Mail: fuhua@mail.tsinghua.edu.cn;
^b State Key Laboratory of Chemical Resource Engineering, Department of Pharmaceutical Engineering, College of Life Science and Technology, Beijing University of Chemical Technology, Beijing 100029, P. R. of China
e-Mail: qiaorz@mail.buct.edu.cn;

Abstract

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Abstract

A simple and efficient copper-catalyzed method for synthesis of fused pyridoquinazolones has been developed without addition of any ligand or additive, and it can tolerate various functional groups.

Key words

N-heterocycle - pyridoquinazolone - copper - synthetic method

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References and Notes

<A NAME="RW09511ST-1">1</A> DeSimone RW. Currie KS. Mitchell SA. Darrow JW. Pippin DA. Comb. Chem. High Throughput Screening 2004, 7: 473

<A NAME="RW09511ST-2">2</A> Leeson PD. Springthorpe B. Nat. Rev. Drug Discovery 2007, 6: 881

<A NAME="RW09511ST-3A">3a</A> Ma Z.-Z. Hano Y. Nomura T. Chen Y.-J. Heterocycles 1997, 46: 541

<A NAME="RW09511ST-3B">3b</A> Yoshida S. Aoyagi T. Harada S. Matsuda N. Ikeda T. Naganawa H. Hamada M. Takeuchi T. J. Antibiot. 1991, 44: 111

<A NAME="RW09511ST-3C">3c</A> Deng Y. Xu R. Ye Y. J. Chin. Pharm. Sci. 2000, 9: 116

<A NAME="RW09511ST-3D">3d</A> Wattanapiromsakul C. Forster PI. Waterman PG. Phytochemistry 2003, 64: 609

<A NAME="RW09511ST-4A">4a</A> Horton DA. Bourne GT. Smythe ML. Chem. Rev. 2003, 103: 893

<A NAME="RW09511ST-4B">4b</A> Mhaske SB. Argade NP. Tetrahedron 2006, 62: 9787 ; and references cited therein

<A NAME="RW09511ST-5">5</A> Sinha S. Srivastava M. Prog. Drug Res. 1994, 43: 143

<A NAME="RW09511ST-6">6</A> de Laszlo SE. Quagliato CS. Greenlee WJ. Patchett AA. Chang RSL. Lotti VJ. Chen T.-B. Scheck SA. Faust KA. Kivlighn SS. Schorn TS. Zingaro GJ. Siegl PKS. J. Med. Chem. 1993, 36: 3207

<A NAME="RW09511ST-7">7</A> Liverton NJ. Armstrong DJ. Claremon DA. Remy DC. Baldwin JJ. Lynch RJ. Zhang G. Gould RJ. Bioorg. Med. Chem. Lett. 1998, 8: 483

<A NAME="RW09511ST-8">8</A> Zhang W. Mayer JP. Hall SE. Weigel JA. J. Comb. Chem. 2001, 3: 255

<A NAME="RW09511ST-9">9</A> Witt A. Bergman J. Curr. Org. Chem. 2003, 7: 659 ; and references cited therein

Selected examples, see:

<A NAME="RW09511ST-10A">10a</A> Griess P. Ber. Dtsch. Chem. Ges. 1869, 2: 415

<A NAME="RW09511ST-10B">10b</A> Griess P. Ber. Dtsch. Chem. Ges. 1878, 11: 1985

<A NAME="RW09511ST-10C">10c</A> von Niementowski S. J. Prakt. Chem. 1895, 51: 564

<A NAME="RW09511ST-10D">10d</A> Liu J.-F. Ye P. Zhang B. Bi G. Sargent K. Yu L. Yohannes D. Baldino CM. J. Org. Chem. 2005, 70: 6339

<A NAME="RW09511ST-10E">10e</A> Liu J.-F. Kaselj M. Isome Y. Ye P. Sargent K. Sprague K. Cherrak D. Wilson CJ. Si Y. Yohannes D. Ng S.-C. J. Comb. Chem. 2006, 8: 7

<A NAME="RW09511ST-10F">10f</A> Roy AD. Subramanian A. Roy R. J. Org. Chem. 2006, 71: 382

<A NAME="RW09511ST-10G">10g</A> Yoo CL. Fettinger JC. Kurth MJ. J. Org. Chem. 2005, 70: 6941

<A NAME="RW09511ST-10H">10h</A> Kamal A. Reddy KS. Prasad BR. Babu AH. Ramana AV. Tetrahedron Lett. 2004, 45: 6517

<A NAME="RW09511ST-10I">10i</A> Larksarp C. Alper H. J. Org. Chem. 2000, 65: 2773

<A NAME="RW09511ST-11A">11a</A> Timári C. Hajós G. Messmer A. J. Heterocycl. Chem. 1990, 27: 2005

<A NAME="RW09511ST-11B">11b</A> Nosova EV. Laeva AA. Trashakhova TV. Golovchenko AV. Lipunova GN. Slepukhin PA. Charushin VN. Russ. J. Org. Chem. 2009, 45: 904

<A NAME="RW09511ST-12">12</A> Nosova V. Liponova GN. Kravchenko MA. Laeva AA. Charushin VN. Pharm. Chem. J. 2008, 42: 169

For recent reviews on copper-catalyzed cross-couplings, see:

<A NAME="RW09511ST-13A">13a</A> Ma D. Cai Q. Acc. Chem. Res. 2008, 41: 1450

<A NAME="RW09511ST-13B">13b</A> Kunz K. Scholz U. Ganzer D. Synlett 2003, 2428

<A NAME="RW09511ST-13C">13c</A> Ley SV. Thomas AW. Angew. Chem. Int. Ed. 2003, 42: 5400

<A NAME="RW09511ST-13D">13d</A> Beletskaya IP. Cheprakov AV. Coord. Chem. Rev. 2004, 248: 2337

<A NAME="RW09511ST-13E">13e</A> Evano G. Blanchard N. Toumi M. Chem. Rev. 2008, 108: 3054

<A NAME="RW09511ST-13F">13f</A> Monnier F. Taillefer M. Angew. Chem. Int. Ed. 2009, 48: 6954

<A NAME="RW09511ST-13G">13g</A> Rao H. Fu H. Synlett 2011, 745 ; and references cited therein

For selected examples:

<A NAME="RW09511ST-13H">13h</A> Klapars A. Antilla JC. Huang X. Buchwald SL. J. Am. Chem. Soc. 2001, 123: 7727

<A NAME="RW09511ST-13I">13i</A> Antilla JC. Klapars A. Buchwald SL. J. Am. Chem. Soc. 2002, 124: 11684

<A NAME="RW09511ST-13J">13j</A> Okano K. Tokuyama H. Fukuyama T. Org. Lett. 2003, 5: 4987

<A NAME="RW09511ST-13K">13k</A> Gujadhur RK. Bates CG. Venkataraman D. Org. Lett. 2001, 3: 4315

<A NAME="RW09511ST-13L">13l</A> Gajare AS. Toyota K. Yoshifuji M. Yoshifuji F. Chem. Commun. 2004, 1994

<A NAME="RW09511ST-13M">13m</A> Ma D. Zhang Y. Yao J. Wu S. Tao F. J. Am. Chem. Soc. 1998, 120: 12459

<A NAME="RW09511ST-13N">13n</A> Ma D. Cai Q. Zhang H. Org. Lett. 2003, 5: 2453

<A NAME="RW09511ST-13O">13o</A> Zhu L. Cheng L. Zhang Y. Xie R. You J. J. Org. Chem. 2007, 72: 2737

For recent studies on the synthesis of N-heterocycles through Ullmann-type couplings, see:

<A NAME="RW09511ST-14A">14a</A> Martin R. Rivero MR. Buchwald SL. Angew. Chem. Int. Ed. 2006, 45: 7079

<A NAME="RW09511ST-14B">14b</A> Evindar G. Batey RA. J. Org. Chem. 2006, 71: 1802

<A NAME="RW09511ST-14C">14c</A> Bonnaterre F. Bois-Choussy M. Zhu J. Org. Lett. 2006, 8: 4351

<A NAME="RW09511ST-14D">14d</A> Zou B. Yuan Q. Ma D. Angew. Chem. Int. Ed. 2007, 46: 2598

<A NAME="RW09511ST-14E">14e</A> Wang B. Lu B. Jiang Y. Ma D. Org. Lett. 2008, 10: 2761

Selected examples for copper-catalyzed cross-couplings, see:

<A NAME="RW09511ST-15A">15a</A> Rao H. Fu H. Jiang Y. Zhao Y. J. Org. Chem. 2005, 70: 8107

<A NAME="RW09511ST-15B">15b</A> Rao H. Jin Y. Fu H. Jiang Y. Zhao Y. Chem. Eur. J. 2006, 12: 3636

<A NAME="RW09511ST-15C">15c</A> Jiang D. Fu H. Jiang Y. Zhao Y. J. Org. Chem. 2007, 72: 672

<A NAME="RW09511ST-15D">15d</A> Guo X. Rao H. Fu H. Jiang Y. Zhao Y. Adv. Synth. Catal. 2006, 348: 2197

<A NAME="RW09511ST-15E">15e</A> Rao H. Fu H. Jiang Y. Zhao Y. Angew. Chem. Int. Ed. 2009, 48: 1114

Selected examples for copper-catalyzed synthesis of N-heterocycles, see:

<A NAME="RW09511ST-16A">16a</A> Liu X. Fu H. Jiang Y. Zhao Y. Angew. Chem. Int. Ed. 2009, 48: 348

<A NAME="RW09511ST-16B">16b</A> Huang C. Fu Y. Fu H. Jiang Y. Zhao Y. Chem. Commun. 2008, 6333

<A NAME="RW09511ST-16C">16c</A> Yang D. Fu H. Hu L. Jiang Y. Zhao Y. J. Org. Chem. 2008, 73: 7841

<A NAME="RW09511ST-16D">16d</A> Yang D. Liu H. Yang H. Fu H. Hu L. Jiang Y. Zhao Y. Adv. Synth. Catal. 2009, 351: 1999

<A NAME="RW09511ST-16E">16e</A> Wang F. Liu H. Fu H. Jiang Y. Zhao Y. Org. Lett. 2009, 11: 2469

<A NAME="RW09511ST-16F">16f</A> Lu J. Gong X. Yang H. Fu H. Chem. Commun. 2010, 46: 4172

<A NAME="RW09511ST-16G">16g</A> Yang X. Fu H. Qiao R. Jiang Y. Zhao Y. Adv. Synth. Catal. 2010, 352: 1033

<A NAME="RW09511ST-16H">16h</A> Gong X. Yang H. Liu H. Jiang Y. Zhao Y. Fu H. Org. Lett. 2010, 12: 3128

General Procedure for the Synthesis of Compounds 2a-n A two-necked, round-bottom flask was charged with a magnetic stirrer, evacuated, and back-filled with nitrogen. Substituted 2-halo-N-(pyridin-2-yl)arylamide (1) (0.5 mmol), Cs₂CO₃ (1 mmol, 326 mg), and toluene (2 mL) were added to the flask. After a 10 min stirring at r.t. under nitrogen atmosphere, CuI (0.025 mmol, 5 mg) was added to the flask. The mixture was stirred at 110 ˚C for 24 or 36 h (see Table [²] in text) under nitrogen atmosphere. After completion of the reaction, the solvent of the resulting mixture was removed with the aid of a rotary evaporator, and the residue was purified by column chromatography on silica gel using PE-EtOAc as eluent to give the desired product.

<A NAME="RW09511ST-18A">18a</A> Nicolaou KC. Boddy CNC. Natarajar S. Yue T.-Y. Li H. Bräse S. Ramanjulu JM. J. Am. Chem. Soc. 1997, 119: 3421

<A NAME="RW09511ST-18B">18b</A> Kalinin AV. Bower JF. Riebel P. Snieckus V. J. Org. Chem. 1999, 64: 2986

<A NAME="RW09511ST-18C">18c</A> Cai Q. Zou B. Ma D. Angew. Chem. Int. Ed. 2006, 45: 1276

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