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Synthesis 2013; 45(21): 2998-3006
DOI: 10.1055/s-0033-1338521
DOI: 10.1055/s-0033-1338521
paper
One-Pot Synthesis of Quinazolinones from Anthranilamides and Aldehydes via p-Toluenesulfonic Acid Catalyzed Cyclocondensation and Phenyliodine Diacetate Mediated Oxidative Dehydrogenation
Further Information
Publication History
Received: 18 June 2013
Accepted after revision: 23 July 2013
Publication Date:
15 August 2013 (online)
Abstract
A variety of 4(3H)-quinazolinones are synthesized conveniently in one pot from 2-aminobenzamides and aldehydes, via cyclization catalyzed by p-toluenesulfonic acid followed by oxidative dehydrogenation mediated by the hypervalent iodine compound phenyliodine diacetate [PhI(OAc)2, PIDA]. Highlights of the described method include the first synthesis of quinazolinones bearing an N-alkoxy substituent, a new application of phenyliodine diacetate as an efficient dehydrogenative oxidant, and mild reaction conditions.
Key words
quinazolinones - cyclocondensation - dehydrogenation - phenyliodine diacetate - one-pot synthesisSupporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis.
- Supporting Information
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References
- 1a Reisch J, Gunaherath G. J. Nat. Prod. 1989; 52: 404
- 1b Liu J, Wilson CJ, Ye P, Sprague K, Sargent K, Si Y, Beletsky G, Yohannes D, Ng S. Bioorg. Med. Chem. Lett. 2006; 16: 686
- 1c Mhaske SB, Argade NP. Tetrahedron 2006; 62: 9787
- 1d Liu J, Kaselj M, Isome Y, Ye P, Sargent K, Sprague K, Cherrak D, Wilson CJ, Si Y, Yohannes D, Ng S. J. Comb. Chem. 2006; 8: 7
- 1e Ma C, Li Y, Niu S, Zhang H, Liu X, Che Y. J. Nat. Prod. 2011; 74: 32
- 1f Nett M, Hertweck C. J. Nat. Prod. 2011; 74: 2265
- 1g Sharma PC, Kaur G, Pahza R, Sharma A, Rajak H. Curr. Med. Chem. 2011; 18: 4786
- 1h Arora R, Kapoor A, Gill NS, Rana AC. Int. Res. J. Pharm. 2011; 2: 22
- 2 Mhaske SB, Argade NP. J. Org. Chem. 2001; 66: 9038
- 3a Chenard BL, Menniti FS, Pagnozzi MJ, Shenk KD, Ewing FE, Welch WM. Bioorg. Med. Chem. Lett. 2000; 10: 1203
- 3b Bhogal N, Balls M. Curr. Drug Discovery Technol. 2008; 5: 250
- 4a Liu J, Ye P, Sprague K, Sargent K, Yohannes D, Baldino CM, Wilson CJ, Ng SC. Org. Lett. 2005; 7: 3363
- 4b Mason JJ, Bergman J. Org. Biomol. Chem. 2007; 5: 2486
- 4c Pospisil P, Korideck H, Wang K, Yang Y, Iyer LK, Kassis AI. Chem. Biol. Drug. Des. 2012; 79: 926
- 4d Rajput R, Mishra AP. Int. J. Pharm. Pharm. Sci. 2012; 4: 66
- 4e Devi KA, Sriram MS. Int. J. Drug Dev. Res. 2012; 4: 324
- 4f Rajiput CS, Bora PS. Int. J. Pharm. Biol. Sci. 2012; 3: 119
- 4g Zhu S, Chandrashekar G, Meng L, Robinson K, Chatterji D. Bioorg. Med. Chem. 2012; 20: 927
- 5a Naleway JJ, Fox C, Robinhold D, Terpetsching E, Olsen NA, Haugland RP. Tetrahedron Lett. 1994; 35: 8569
- 5b Lopez SE, Rosales ME, Urdaneta N, Godoy MV, Charris JE. J. Chem. Res., Synop. 2000; 6: 258
- 5c Bhat BA, Sahu DP. Synth. Commun. 2004; 34: 2169
- 5d Abdel-Jalil RJ, Voelterb W, Saeed M. Tetrahedron Lett. 2004; 45: 3475
- 5e Abiri M, Salehi P, Mohammadi A, Baghbanzadeh M. Synth. Commun. 2005; 35: 279
- 5f Liu J, Lee J, Dalton AM, Bi G, Yu L, Baldino CM, McElory E, Brown M. Tetrahedron Lett. 2005; 46: 1241
- 5g Salehi P, Dabiri M, Zolfigol MA, Baghbanzadeh M. Tetrahedron Lett. 2005; 46: 7051
- 5h Bakavoli M, Sabzevari O, Rahimizadeh M. Chin. Chem. Lett. 2007; 18: 1466
- 5i Zhou J, Fu L, Lv M, Liu J, Pei D, Ding K. Synthesis 2008; 3974
- 5j Bakavoli M, Shiri A, Ebrahimpour Z, Rahimzadeh M. Chin. Chem. Lett. 2008; 19: 1403
- 5k Baghbanzadeh M, Dabiri M, Salehi P. Heterocycles 2008; 75: 2809
- 5l Chen J, Wu D, He F, Liu M, Wu H, Ding J, Su W. Tetrahedron Lett. 2008; 49: 3814
- 5m Zeng L, Cai C. J. Heterocycl. Chem. 2010; 47: 1035
- 5n Dabiri M, Salehi P, Bahramnejad M, Alizadeh M. Monatsh. Chem. 2010; 141: 877
- 5o Xu W, Fu H. J. Org. Chem. 2011; 76: 3846
- 5p Zhou J, Fang J. J. Org. Chem. 2011; 76: 7730
- 5q Xu W, Jin Y, Liu H, Jing Y, Fu H. Org. Lett. 2011; 13: 1274
- 5r Wu X, Schranck J, Neumann H, Beller M. Chem. Eur. J. 2011; 17: 12246
- 5s Hikawa H, Ino Y, Suzuki H, Yokoyama Y. J. Org. Chem. 2012; 77: 7046
- 5t Li B, Samp L, Sagal J, Hayward CM, Yang C, Zhang Z. J. Org. Chem. 2013; 78: 1273
- 6 Davoodnia A, Allameh S, Fakhari AR, Tavakoli-Hoseini A. Chin. Chem. Lett. 2010; 21: 550
- 7a Mamalis P, Rix MJ, Sarsfield AA. J. Chem. Soc. 1965; 6278
- 7b Schapira CB, Lamdan S. J. Heterocycl. Chem. 1972; 9: 569
- 7c Katritzky AR, Brown SB. Synthesis 1978; 619
- 7d Katritzky AR, Cook MJ, Brown SB, Cruz R, Millet GH, Anani A. J. Chem. Soc., Perkin Trans. 1 1979; 2493
- 8a Stephensen PU, Bonnesen C, Schaldach C, Andersen O, Bjeldanes LF, Vang O. Nutr. Cancer 2000; 36: 112
- 8b Tsotinis A, Eleutheriades A, Hough K, Sugden D. Chem. Commun. 2003; 382
- 8c Neave AS, Sarup SM, Seidelin M, Duss F, Vang O. Toxicol. Sci. 2005; 83: 126
- 9a Moriarty RM. J. Org. Chem. 2005; 70: 2893
- 9b Ciufolini MA, Braun NA, Canesi S, Ousmer M, Chang J, Chai D. Synthesis 2007; 3759
- 9c Zhdankin VV, Stang PJ. Chem. Rev. 2008; 108: 5299
- 9d Zhdankin VV. ARKIVOC 2009; (i): 1
- 9e Kita Y, Dohi T. Chem. Commun. 2009; 2073
- 9f Silva L, Olofsson B. Nat. Prod. Rep. 2011; 28: 1722
- 10a Kikugawa Y, Nagashima A, Sakamoto T, Miyazawa E, Shiiya M. J. Org. Chem. 2003; 68: 6739
- 10b Correa A, Tellitu I, Domínguez E, SanMartin R. J. Org. Chem. 2006; 71: 8316
- 10c Tellitu I, Urrejola A, Serna S, Moreno I, Herrero MT, Domínguez E, SanMartin R, Correa A. Eur. J. Org. Chem. 2007; 437
- 10d Malamidou-Xenikaki E, Spyroudis S, Tsanakopoulou M, Hadjipavlou-Litina D. J. Org. Chem. 2009; 74: 7315
- 10e Liang H, Ciufolini MA. Tetrahedron 2010; 66: 5884
- 10f Lovick HM, Michael FE. J. Am. Chem. Soc. 2010; 132: 1249
- 10g Cho S, Yoon J, Chang S. J. Am. Chem. Soc. 2011; 133: 5996
- 10h Fujita M, Wakita M, Sugimura T. Chem. Commun. 2011; 47: 3983
- 10i Antonchick AP, Samanta R, Kulikov K, Lategahn J. Angew. Chem. Int. Ed. 2011; 50: 8605
- 10j Zhong W, Yang J, Meng X, Li Z. J. Org. Chem. 2011; 76: 9997
- 10k Kang Y.-B, Gade LH. J. Org. Chem. 2012; 77: 1610
- 10l Zhong W, Liu S, Yang J, Meng X, Li Z. Org. Lett. 2012; 14: 3336
- 10m Kim HJ, Cho SH, Chang S. Org. Lett. 2012; 14: 1424
- 10n Samanta R, Bauer JO, Strohmann C, Antonchick AP. Org. Lett. 2012; 14: 5518
- 10o Yu Z, Ma L, Yu W. Synlett 2012; 23: 1534
- 10p Tian T, Zhong W, Meng S, Meng X, Li Z. J. Org. Chem. 2013; 78: 728
- 10q Alla SK, Kumar RK, Sadhu P, Punniyamurthy T. Org. Lett. 2013; 15: 1334
- 10r Nocquet-Thibault S, Retailleau P, Cariou K, Dodd RH. Org. Lett. 2013; 15: 1842
- 11a Correa A, Tellitu I, Domínguez E, SanMartin R. Tetrahedron 2006; 62: 11100
- 11b Correa A, Tellitu I, Domínguez E, SanMartin R. J. Org. Chem. 2006; 71: 3501
- 11c Correa A, Tellitu I, Domínguez E, SanMartin R. Org. Lett. 2006; 8: 4811
- 11d Huang J, Lu Y, Qiu B, Liang Y, Dong D. Synthesis 2007; 2791
- 11e Wang K, Fu X, Liu J, Liang Y, Dong D. Org. Lett. 2009; 11: 1015
- 12a Kita Y, Arisawa M, Gyoten M, Nakajima M, Hamada R, Tohma H, Takada T. J. Org. Chem. 1998; 63: 6625
- 12b Dohi T, Morimoto K, Kiyono Y, Maruyama A, Tohma H, Kita Y. Chem. Commun. 2005; 2930
- 12c Dohi T, Morimoto K, Maruyama A, Kita Y. Org. Lett. 2006; 8: 2007
- 12d Kita Y, Morimoto K, Ito M, Ogawa C, Goto A, Dohi T. J. Am. Chem. Soc. 2009; 131: 1668
- 12e Gu Y, Wang D. Tetrahedron Lett. 2010; 51: 2004
- 12f Samanta R, Lategahn J, Antonchick AP. Chem. Commun. 2012; 48: 3194
- 12g Jacquemot G, Canesi S. J. Org. Chem. 2012; 77: 7588
- 13a Du Y, Liu R, Linn G, Zhao K. Org. Lett. 2006; 8: 5919
- 13b Yu W, Du Y, Zhao K. Org. Lett. 2009; 11: 2417
- 14 Li X, Du Y, Liang Z, Li X, Pan Y, Zhao K. Org. Lett. 2009; 11: 2643
- 15 Ban X, Pan Y, Lin Y, Wang S, Du Y, Zhao K. Org. Biomol. Chem. 2012; 10: 3606
- 16a Zhao F, Liu X, Qi R, Zhang-Negrerie D, Huang J, Du Y, Zhao K. J. Org. Chem. 2011; 76: 10338
- 16b Zheng Y, Li X, Ren C, Zhang-Negrerie D, Du Y, Zhao K. J. Org. Chem. 2012; 77: 10353
- 16c Liu X, Cheng R, Zhang-Negrerie D, Du Y, Zhao K. Org. Lett. 2012; 14: 5480
- 17 Guengoer T, Chen Y, Golla R, Ma Z, Corte JR, Northrop JP, Bin B, Dickson JK, Stouch T, Zhou R, Johnson SE, Seethala R, Feyen JH. J. Med. Chem. 2006; 49: 2440
- 18 Morgentin R, Barlaam B, Foote K, Hassall L, Hawkins J, Jones CD, Le Griffon A, Peru A, Ple P. Synth. Commun. 2012; 42: 8
- 19 Deore R, Chen G, Chang P, Chern T, Lai S, Chuang M, Lin J, Kung F, Chen C, Chiou C, Chern J. ChemMedChem 2012; 7: 850
- 20 Weinberg LR, Albom MS, Angeles TS, Husten J, Lisko JG, McHugh RJ, Milkiewicz K, Murthy S, Ott GR, Theroff JP, Tripathy R, Underiner TL, Zificsak CA, Dorsey BD. Bioorg. Med. Chem. Lett. 2011; 21: 164
- 21 Bonne D, Dekhane M, Zhu J. Org. Lett. 2005; 7: 5285
- 22 Chauhan J, Fletcher S. Tetrahedron Lett. 2012; 53: 4951
- 23 Petrov JS, Andreev GN. Org. Prep. Proced. Int. 2005; 37: 560
- 24 Shaterian HR, Oveisi AR, Honarmand M. Synth. Commun. 2010; 40: 1231
- 25 Snider BB, Zeng H. Heterocycles 2003; 61: 173
- 26 Liu J, Lee J, Dalton AM, Bi G, Yu L, Baldino CM, McElory E, Brown M. Tetrahedron Lett. 2005; 46: 1241
- 27 Xu L, Jiang Y, Ma D. Org. Lett. 2012; 14: 1150
For selected examples, see:
For selected examples, see:
For selected examples, see:
For recent reviews, see:
For recent examples of carbon–heteroatom bond formation using hypervalent iodine(III) reagents, see:
For recent examples of heteroatom–heteroatom bond formation using hypervalent iodine(III) reagents, see:
For selected examples of carbon–carbon bond formation using hypervalent iodine(III) reagents, see: