Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Synthesis 2013; 45(24): 3349-3354
DOI: 10.1055/s-0033-1340040
DOI: 10.1055/s-0033-1340040
paper
Copper-Catalyzed Domino Synthesis of Quinazolin-4(3H)-ones from (Hetero)arylmethyl Halides, Bromoacetate, and Cinnamyl Bromide
Further Information
Publication History
Received: 21 August 2013
Accepted after revision: 23 September 2013
Publication Date:
18 October 2013 (online)
Abstract
Alkyl halides, including heteroarylmethyl and arylmethyl halides, bromoacetate, and cinnamyl bromide, are readily prepared via halogenation from basic raw materials, even using green processes. It is essential to replace their downstream products with them to prepare medicinally important heterocycles quinazolin-4(3H)-ones. Copper(I) bromide catalyzed domino reaction of alkyl halides and anthranilamides under air affords 2-substituted quinazolin-4(3H)-ones in good to excellent yields and with wide functional group tolerance. A mechanism for a copper(I) bromide involved organometal-catalyzed reaction via a four-step domino reaction is proposed.
Supporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis.
- Supporting Information
-
References
- 1a Eguchi S. Top. Heterocycl. Chem. 2006; 6: 113
- 1b Demeunynck M, Baussanne I. Curr. Med. Chem. 2013; 20: 794
- 2 Liang JL, Cha HC, Jahng Y. Molecules 2011; 16: 4861
- 3 Chen AL, Chen KK. J. Am. Pharm. Assoc. 1933; 22: 716
- 4 Xia Y, Yang ZY, Hour MJ, Kuo SC, Xia P, Bastow KF, Nakanishi Y, Nampoothiri P, Hackl T, Hamel E, Lee KH. Bioorg. Med. Chem. Lett. 2001; 11: 1193
- 5 Alagarsamy V, Raja SV, Dhanabal K. Bioorg. Med. Chem. 2007; 15: 235
- 6 Selvam P, Girija K, Nagarajan G, De Clercq E. Indian J. Pharm. Sci. 2005; 67: 484
- 7 Alagarsamy V, Pathak US. Bioorg. Med. Chem. 2007; 15: 3457
- 8 Jang CS, Fu FY, Wang CY, Huang KC, Lu G, Thou TC. Science (Washington, D.C.) 1946; 103: 59
- 9 Kuneš J, Bažant J, Pour M, Waisser K, Šlosárek M, Janota J. Farmaco 2000; 55: 725
- 10 Letourneau J, Riviello C, Ho K.-K, Chan J.-H, Ohlmeyer M, Jokiel P, Neagu I, Morphy JR, Napier SE. WO 2006095014, 2006
- 11 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
- 12 Potewar TM, Nadaf RN, Daniel T, Lahoti RJ, Srinivasan KV. Synth. Commun. 2005; 35: 231
- 13 Zhang X, Ye D, Sun H, Guo D, Wang J, Huang H, Zhang X, Jiang H, Liu H. Green Chem. 2009; 11: 1881
- 14 Takeuchi H, Haguvara S, Eguchi S. Tetrahedron 1989; 45: 6375
- 15 Xu W, Jin Y, Liu H, Jiang Y, Fu H. Org. Lett. 2011; 13: 1274
- 16a Zhan D, Li T, Wei H, Weng W, Ghandi K, Zeng Q. RSC Adv. 2013; 3: 9325
- 16b Abdel-Jalil RJ, Voelter W, Saeed M. Tetrahedron Lett. 2004; 45: 3475
- 17 Zhou J, Fang J. J. Org. Chem. 2011; 76: 7730
- 18 Couture A, Cornet H, Grandclaudon P. Synthesis 1991; 1009
- 19 Connolly DJ, Guiry PJ. Synlett 2001; 1707
- 20 Croce PD, Ferraccioli R, La Rosa C. Heterocycles 1997; 45: 1309
- 21 Chen J, Wu D, He F, Liu M, Wu H, Ding J, Su W. Tetrahedron Lett. 2008; 49: 3814
- 22 Mohammadi AA, Sadat Hossini SS. Chin. J. Chem. 2011; 29: 1982
- 23a Tanko JM, Blackert JF. Science (Washington, D.C.) 1994; 263: 203
- 23b Hunter WH, Edgar DE. J. Am. Chem. Soc. 1932; 54: 2025
- 24a Mestres R, Palenzuela J. Green Chem. 2002; 4: 314
- 24b Adimurthy S, Ghosh S, Patoliya PU, Ramachandraiah G, Agrawal M, Gandhi MR, Upadhyay SC, Ghosh PK, Ranu BC. Green Chem. 2008; 10: 232
- 25 Nishinaga A, Yamazaki S, Matsuura T. Tetrahedron Lett. 1988; 29: 4115
- 26 Murahashi S.-I, Okano Y, Sato H, Nakae T, Komiya N. Synlett 2007; 1675
- 27a Dong J, Wang Y, Xiang Q, Lv X, Weng W, Zeng Q. Adv. Synth. Catal. 2013; 355: 692
- 27b Dai C, Sun XF, Tu XZ, Wu L, Zhan D, Zeng Q. Chem. Commun. 2012; 48: 5367
- 27c Sun X, Tu X, Dai C, Zhang X, Zhang B, Zeng Q. J. Org. Chem. 2012; 77: 4454
- 27d Zeng Q, Gao Y, Dong J, Weng W, Zhao Y. Tetrahedron: Asymmetry 2011; 22: 717
- 28 Markó IE, Giles PR, Tsukazaki M, Brown SM, Urch CJ. Science (Washington, D.C.) 1996; 274: 2044
- 29 Rhee HK, Yoo JH, Lee E, Kwon YJ, Lee YS, Choo H.-YP, Seo HR. Eur. J. Med. Chem. 2011; 46: 3900
- 30 Hisano T, Ichikawa M, Nakagawa A, Tsuji M. Chem. Pharm. Bull. 1975; 23: 1910
- 31 Lazzaro JT, Paternain AV, Lerma J, Chenard BL, Ewing FE, Huang J, Welch WM, Ganong AH, Menniti FS. Neuropharm 2002; 42: 143
- 32 Ma B, Wang Y, Peng J, Zhu Q. J. Org. Chem. 2011; 76: 6362
- 33 Chandrika PM, Yakaiah T, Narsaiah B, Gayatri G, Kumar KP, Murthy US. N, Rao AR. R. Eur. J. Med. Chem. 2010; 45: 78
- 34 Tavakoli-Hoseini N, Davoodnia A. Synth. React. Inorg., Met.-Org., Nano-Met. Chem. 2012; 42: 76
- 35 Flanagan SP, Goddard R, Guiry PJ. Tetrahedron 2005; 61: 9808
- 36 Baker BR, Almaula PI. J. Org. Chem. 1962; 27: 4672
- 37 Trashakhova TV, Nosova EV, Valova MS, Slepukhin PA, Lipunova GN, Charushin VN. Russian J. Org. Chem. 2011; 47: 753
- 38 El-Azab AS, Al-Omar MA, Abdel-Aziz AA.-M, Abdel-Aziz NI, El-Sayed MA.-A, Aleisa AM, Sayed-Ahmed MM, Abdel-Hamide SG. Eur. J. Med. Chem. 2010; 45: 4188