Yb(OTf)3-Catalyzed One-Pot Synthesis of Quinazolin-4(3H)-ones from Anthranilic­ Acid, Amines and Ortho Esters (or Formic Acid) in Solvent-Free Conditions

Limin Wang; Jianjun Xia; Fang Qin; Changtao Qian; Jie Sun

doi:10.1055/s-2003-39397

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Synthesis 2003(8): 1241-1247
DOI: 10.1055/s-2003-39397

PAPER

Yb(OTf)₃-Catalyzed One-Pot Synthesis of Quinazolin-4(3H)-ones from Anthranilic Acid, Amines and Ortho Esters (or Formic Acid) in Solvent-Free Conditions

Limin Wang*^a, Jianjun Xia^a, Fang Qin^a, Changtao Qian^b, Jie Sun^b
^a Institute of Fine Chemicals, East China University of Science and Technology, 130 Meilong Lu, Shanghai 200237, P. R. China
Fax: +86(21)64252288; e-Mail: wanglimin@ecust.edu.cn, wcathy@china.com;
^b Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032, P. R. China

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Publication History

Received 20 November 2002
Publication Date:
26 May 2003 (online)

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Abstract

An efficient synthesis of an array of quinazolin-4(3H)-ones from anthranilic acid, ortho esters (or formic acid) and amines using Yb(OTf)₃ in one-pot under solvent-free conditions is described. Compared with the classical reaction conditions, this new synthetic method has the advantage of excellent yields (75-99%), shorter reaction time (few minutes) and reusability of the catalyst.

Key words

quinazolin-4(3H)-ones - ytterbium triflate - one-pot reaction - anthranilic acid - amine

References

1 Widdege A. J. Prakt. Chem. 1887, 36: 141

Google Scholar
2a Baker BR. Schaub RE. Joseph JP. McEvoy FJ. Williams JH. J. Org. Chem. 1953, 18: 133

Google Scholar
2b Armarego WLF. Adv. Heterocycl. Chem. 1979, 24: 1

Google Scholar
2c Wolfe JF. Rathman TL. Sleevi MC. Campbell JA. Greenwood TD. J. Med. Chem. 1990, 33: 161

Google Scholar
2d Gravier D. Dupin JP. Casadebaig F. Hou G. Boisseau M. Bernard H. Pharmazie 1992, 47: 91

Google Scholar
2e Leoni O. Bernardi R. Gueyrard D. Rollin P. Palmieri S. Tetrahedron: Asymmetry 1999, 10: 4775

Google Scholar
2f Gueyrard D. Grumel V. Leoni O. Palmieri S. Rollin P. Heterocycles 2000, 52: 827

Google Scholar
2g Terashima K. Shimamura H. Kawase A. Tanaka Y. Tanimura T. Kamisaki T. Ishizuka Y. Sato M. Chem. Pharm. Bull. 1995, 43: 2021

Google Scholar
2h Kurogi Y. Inoue Y. Tsutsumi K. Nakamura S. Nagao K. Yohsitsugu H. Tsuda Y. J. Med. Chem. 1996, 39: 1433

Google Scholar
2i Liverton NJ. Armstrong DJ. Claremon DA. Remy DC. Baldwin JJ. Lynch RJ. Zhang G. Gould R. Bioorg. Med. Chem. Lett. 1998, 8: 483

Google Scholar
2j Padia JK. Field M. Hinton J. Meecham K. Pablo J. Pinnock R. Roth BD. Singh L. Suman-Chauhan N. Trivedi BK. Webdale L. J. Med. Chem. 1998, 41: 1042

Google Scholar
2k Kamal A. Ramana KV. Rao MV. J. Org. Chem. 2001, 66: 997

Google Scholar
2l Purohit DM. Shah VH. Indian J. Heterocycl. Chem. 1999, 8: 213

Google Scholar
2m Patel NB. Lilakar JD. Indian J. Heterocycl. Chem. 2001, 11: 85

Google Scholar
3a Kuehl FA. Spencer CF. Folkers K. J. Am. Chem. Soc. 1948, 70: 2091

Crossref Google Scholar
3b Kobayashi S. Ueno M. Suzuki R. Ishitani H. Tetrahedron Lett. 1999, 40: 2175

Crossref Google Scholar
4 Tokaya Y. Tasaka H. Chiba T. Uwai K. Tanitsu M. Kim H.-S. Wataya Y. Miura M. Takeshita M. Oshima Y. J. Med. Chem. 1999, 42: 3163

Crossref Google Scholar
5a Rewcastle GW. Denny WA. Bridges AJ. Zhou H. Cody DR. McMichael A. Fry DW. J. Med. Chem. 1995, 38: 3482

Crossref Google Scholar
5b Bridges AJ. Zhou H. Cody DR. Rewcastle GW. McMichael A. Showalter HDH. Fry DW. Kraker AJ. Denny WA. J. Med. Chem. 1996, 39: 267

Crossref Google Scholar
6 Rosowsky A. Mota CE. Wright JE. Queener SF. J. Med. Chem. 1994, 37: 4522

Crossref Google Scholar
7a Jiang JB. Hesson DP. Dusak BA. Dexter DL. Kang GJ. Hamel E. J. Med. Chem. 1990, 33: 1721

Google Scholar
7b Hour M.-J. Huang L.-J. Kuo S.-C. Xia Y. Bastow K. Nakanishi Y. Hamel E. Lee K.-H. J. Med. Chem. 2000, 43: 4479

Google Scholar
8a Brown DJ. England BT. Aust. J. Chem. 1968, 21: 2813

Crossref Google Scholar
8b Sasse K. Synthesis 1978, 379

Crossref Google Scholar
8c Zumbrum A. Lamberth C. Schaub F. Synth. Commun. 1998, 28: 475

Crossref Google Scholar
8d Villagordo JM. Obrecht D. Chucholowsky A. Synlett 1998, 1405

Crossref Google Scholar
8e Ibrahim SS. Abdel-Halim AM. Gabr Y. El-Edfawy S. Abdel-Rahman RM. Indian J. Chem., Sect. B 1998, 37: 62

Crossref Google Scholar
8f Dai X. Wong A. Virgil SC. J. Org. Chem. 1998, 63: 2597

Crossref Google Scholar
8g Yang R.-Y. Kaplan A. Tetrahedron Lett. 2000, 41: 7005

Crossref Google Scholar
8h Witt A. Bergman J. Tetrahedron 2000, 56: 7245

Crossref Google Scholar
8i Yu Y. Ostresh JM. Houghten RA. J. Org. Chem. 2002, 67: 5831

Crossref Google Scholar
8j Lindsay DM. Dohle W. Jensen AE. Kopp F. Knochel P. Org. Lett. 2002, 4: 1819

Crossref Google Scholar
8k Sugimoto O. Yamauchi Y. Tanji K.-I. Heterocycles 2002, 57: 323

Crossref Google Scholar
9a Errede LA. MeBrady JJ. Oien HT. J. Org. Chem. 1977, 42: 656

Google Scholar
9b Rastogi VK. Parmar SS. Singh SP. Akers TK. J. Heterocyl. Chem. 1978, 15: 497

Google Scholar
9c Kornet MJ. Varia T. Beaven W. J. Heterocycl. Chem. 1983, 20: 1553

Google Scholar
9d Parkanyi C. Yuan HL. Stromberg BHE. Evenzahav A. J. Heterocycl. Chem. 1992, 29: 749

Google Scholar
10 Zentmyer DT. Wagner EC. J. Org. Chem. 1949, 14: 967

Crossref Google Scholar
11 Bain DI. Smalley RK. J. Chem. Soc. (C) 1968, 1593

Crossref Google Scholar
12 Papadopoulos EP. Torres CD. Heterocycles 1982, 19: 1039

Google Scholar
13 Eckroth DR. Squire RH. J. Org. Chem. 1971, 36: 224

Google Scholar
14 Khajavi MS. Montazari N. Hosseini SS. J. Chem. Res., Synop. 1997, 286

Google Scholar
15 Bogert MT. Gortner RA. J. Am. Chem. Soc. 1910, 32: 119

Crossref Google Scholar
16a Baker BR. Almaula PI. J. Org. Chem. 1962, 27: 4672

Google Scholar
16b Alemagna A. Buttero PD. Licandro E. Maiorana S. Guastini C. J. Chem. Soc., Chem. Commun. 1983, 337

Google Scholar
16c Süsse M. Adler F. Johne S. Helv. Chim. Acta. 1986, 69: 1017

Google Scholar
17 Mori M. Kobayashi H. Kimura M. Ban Y. Heterocycles 1985, 23: 2803

Google Scholar
18 Onaka T. Tetrahedron Lett. 1971, 4387

Google Scholar
19 Kametani T. Loc CV. Higa T. Koizumi M. Ihara M. Fukumoto K. J. Am. Chem. Soc. 1977, 99: 2306

Crossref Google Scholar
20a Sauter F. Fröhlic J. Blasl K. Gewald K. Heterocycles 1995, 40: 851

Google Scholar
20b Prashad M. Chen L. Repic O. Blacklock TJ. Synth. Commun. 1998, 28: 2125

Google Scholar
21 Connolly DJ. Guiry PJ. Synlett 2001, 1707

Article in Thieme Connect Google Scholar
22 Gueyrard D. Leoni O. Palmieri S. Rollin P. Tetrahedron: Asymmetry 2001, 12: 337

Crossref Google Scholar
23 Moghadam KR. Khajavi MS. J. Chem. Res., Synop. 1998, 702

Crossref Google Scholar
24 Hall N. Science 1994, 266: 32

Crossref Google Scholar
25 Kobayashi S. Hachiya I. Ishitani H. Araki M. Synlett 1993, 472

Article in Thieme Connect Google Scholar
26 Kawada A. Mitamura S. Kobayashi S. Synlett 1994, 545

Article in Thieme Connect Google Scholar
27 Qian C. Huang T. Tetrahedron Lett. 1997, 38: 6721

Crossref Google Scholar
28 Song CE. Shim WH. Roh EJ. Lee S. Choi JH. Chem. Commun. 2001, 1122

Google Scholar
29 Komoto I. Kobayashi S. Chem. Commun. 2001, 1842

Google Scholar
30a Lee S. Park JH. Kang J. Lee JK. Chem. Commun. 2001, 1698

Crossref Google Scholar
30b Wang LC. Qian C. Tetrahedron 2000, 56: 7193

Crossref Google Scholar
30c Chen R. Qian C. Vries JG. Tetrahedron Lett. 2001, 42: 6919

Crossref Google Scholar
30d Huang T. Li CJ. Tetrahedron Lett. 2000, 41: 6715

Crossref Google Scholar
30e Chen R. Qian C. Vries JG. Sun PP. Wang LM. Chin. J. Chem. 2001, 19: 1225 ; Chem. Abstr. 2002, 136, 262860

Crossref Google Scholar
30f Sun PP. Qian C. Wang LM. Chen R. Synth. Commun. 2002, 32: 2973

Crossref Google Scholar
30g Wang LM. Qian C. Tian H. Ma Y. Synth. Commun. 2003, 33: 1459

Crossref Google Scholar
31 Ma Y. Qian C. Wang LM. Yang M. J. Org. Chem. 2000, 65: 3864

Crossref Google Scholar
32 Errede LA. McBrady JJ. Oien HT. J. Org. Chem. 1977, 42: 656

Crossref Google Scholar