One-Pot Synthesis of Quinazolinones from Anthranilamides and Aldehydes via p-Toluenesulfonic Acid Catalyzed Cyclocondensation and Phenyliodine Diacetate Mediated Oxidative Dehydrogenation

Ran Cheng; Tianjian Guo; Daisy Zhang-Negrerie; Yunfei Du; Kang Zhao

doi:10.1055/s-0033-1338521

Synthesis, Inhaltsverzeichnis

Synthesis 2013; 45(21): 2998-3006
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

Autor*innen

Ran Cheng

Tianjin Key Laboratory for Modern Drug Delivery & High-Efficiency, School of Pharmaceutical Science and Technology, Tianjin University, Tianjin 300072, P. R. of China Fax: +86(22)27404031 eMail: duyunfeier@tju.edu.cn eMail: kangzhao@tju.edu.cn
Tianjian Guo

Tianjin Key Laboratory for Modern Drug Delivery & High-Efficiency, School of Pharmaceutical Science and Technology, Tianjin University, Tianjin 300072, P. R. of China Fax: +86(22)27404031 eMail: duyunfeier@tju.edu.cn eMail: kangzhao@tju.edu.cn
Daisy Zhang-Negrerie

Tianjin Key Laboratory for Modern Drug Delivery & High-Efficiency, School of Pharmaceutical Science and Technology, Tianjin University, Tianjin 300072, P. R. of China Fax: +86(22)27404031 eMail: duyunfeier@tju.edu.cn eMail: kangzhao@tju.edu.cn
Yunfei Du*

Tianjin Key Laboratory for Modern Drug Delivery & High-Efficiency, School of Pharmaceutical Science and Technology, Tianjin University, Tianjin 300072, P. R. of China Fax: +86(22)27404031 eMail: duyunfeier@tju.edu.cn eMail: kangzhao@tju.edu.cn
Kang Zhao*

Tianjin Key Laboratory for Modern Drug Delivery & High-Efficiency, School of Pharmaceutical Science and Technology, Tianjin University, Tianjin 300072, P. R. of China Fax: +86(22)27404031 eMail: duyunfeier@tju.edu.cn eMail: kangzhao@tju.edu.cn

Abstract

Alle Artikel dieser Rubrik

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 synthesis

Volltext

Referenzen

References

For selected examples, see:

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

For selected examples, see:

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

For selected examples, see:

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

For recent reviews, see:

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

For recent examples of carbon–heteroatom bond formation using hypervalent iodine(III) reagents, see:

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

For recent examples of heteroatom–heteroatom bond formation using hypervalent iodine(III) reagents, see:

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

For selected examples of carbon–carbon bond formation using hypervalent iodine(III) reagents, see:

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

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