Microwave-Accelerated Dimroth Rearrangement for the Synthesis of Pyrido [2, 3-d]pyrimidin-4-amine Derivatives

doi:10.6023/cjoc201711028

Chin. J. Org. Chem. ›› 2018, Vol. 38 ›› Issue (5): 1165-1171.DOI: 10.6023/cjoc201711028 Previous Articles Next Articles

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微波促进的Dimroth重排反应合成吡啶并[2,3-d]嘧啶-4-胺衍生物

纵朝阳^a,b, 顾惠雯^b, 张立洁^c, 金煜东^a, 孙雅泉^a,b,c

a 盐城师范学院药学院盐城 224007;
b 南京工业大学化工学院南京 210000;
c 江苏海洋产业研究院盐城 224051

收稿日期:2017-11-19 修回日期:2018-01-03 发布日期:2018-01-26
通讯作者: 孙雅泉,E-mail:sunyaquan@hotmail.com E-mail:sunyaquan@hotmail.com
基金资助:
江苏省前瞻科研项目（No.BY2016066-02）和大学生创新（No.201410324014Z）资助项目.

Microwave-Accelerated Dimroth Rearrangement for the Synthesis of Pyrido [2, 3-d]pyrimidin-4-amine Derivatives

Zong Chaoyang^a,b, Gu Huiwen^b, Zhang Lijie^c, Jin Yudong^a, Sun Yaquan^a,b,c

a School of Pharmacy, Yancheng Teachers University, Yancheng 224007;
b Institute of Chemical Technology, Nanjing Tech University, Nanjing 210000;
c Jiangsu Marine Industry Research Institute, Yancheng 224051

Received:2017-11-19 Revised:2018-01-03 Published:2018-01-26
Contact: 10.6023/cjoc201711028 E-mail:sunyaquan@hotmail.com
Supported by:
Project supported by the Jiangsu Prospective Joint Research Project (No. BY2016066-02) and the College Students Innovation Project (No. 201410324014Z).

1. Microwave-Accelerated Dimroth Rearrangement for the Synthesis of Pyrido [2, 3-d]pyrimidin-4-amine Derivatives.PDF(2702KB)

Abstract

In this paper, a novel synthetic method for N-(3, 5-dichlorophenyl)pyrido [2, 3-d]pyrimidin-4-amine was reported, which began from 2-aminonicotinonitrile, following condensation, cyclization and then Dimroth rearrangement reaction under microwave irradiation conditions. The over yield was 90%. Employing the same synthetic method, 20 pyrido [2, 3-d]pyrimidin- 4-amine derivatives were synthesized. We also compared microwave irradiation and oil bath heating for synthetizing the target products. The results showed that the method under microwave irradiation for the preparation of pyrido [2, 3-d]pyrimidin- 4-amine was time-saving and high yield. It is expected to become an efficient, gentle and environmentally friendly synthetic method of pyrido [2, 3-d]pyrimidin-4-amine.

Key words: pyrido[2, 3-d]pyrimidin-4-amine, Dimroth rearrangement, organic synthesis, microwave irradiation

Cite this article

Zong Chaoyang, Gu Huiwen, Zhang Lijie, Jin Yudong, Sun Yaquan. Microwave-Accelerated Dimroth Rearrangement for the Synthesis of Pyrido [2, 3-d]pyrimidin-4-amine Derivatives[J]. Chin. J. Org. Chem., 2018, 38(5): 1165-1171.

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[1] Li, M.; Liu, R.; Tian, Y; Chang, Y.; Xiao, Y. Chin. J. Chem. 2017, 35, 1405.
[2] Jia, T.; Zheng, N.; Cai, W.; Ying, L.; Huang, F. Acta Chim. Sinica 2017, 75, 808(in Chinese). (贾涛, 郑楠楠, 蔡万清, 应磊, 黄飞, 化学学报, 2017, 75, 808.)
[3] Lin, W.; Hu, X.; Wang, Y.; Song, S.; Zhang, M.; Shi, D. Chin. J. Org. Chem. 2018, 38, 855(in Chinese). (林伟, 胡秀秀, 王雅珍, 宋帅, 张梦烨, 史达清, 有机化学, 2018, 38, 855.)
[4] Zhang, B.; Yang, L.; Shi, R.; Kang, Y. Chin. J. Org. Chem. 2016, 36, 352(in Chinese). (张变香, 杨丽花, 史瑞雪, 亢永强, 有机化学, 2016, 36, 352.)
[5] Insuasty, D.; Abonia, R.; Insuasty, B.; Quiroga, J.; Laali, K. K.; Nogueras, M.; Cobo, J. ACS Comb. Sci. 2017, 19, 555.
[6] Mamaghani, M.; Hossein Nia, R. J. Heterocycl. Chem. 2017, 54, 1700.
[7] Satham, L.; Namboothiri, I. N. N. J. Org. Chem. 2017, 82, 6482.
[8] Hou, J.; Wan, S. H.; Wang, G. F.; Zhang, T. T.; Li, Z. H.; Tian, Y. X.; Yu, Y. H.; Wu, X. Y.; Zhang, J. J. Eur. J. Med. Chem. 2016, 118, 276.
[9] Saurat, T.; Buron, F.; Rodrigues, N.; Tauzia de, M.; Colliandre, L.; Bourg, S.; Bonnet, P.; Guillaumet, G.; Akssira, M.; Corlu, A.; Guillouzo, C.; Berthier, P.; Rio, P.; Jourdan, M.; Benedetti, M.; Routier, S. J. Med. Chem. 2014, 57, 613.
[10] Zhang, H. J.; Wang, S. B.; Wen, X.; Li, J. Z.; Quan, Z. S. Med. Chem. Res. 2016, 25, 1287.
[11] Lacbay, C. M.; Mancuso, J.; Lin, Y. S.; Bennett, N; Gotte, M.; Tsantrizos, Y. S. J. Med. Chem. 2014, 57, 7435.
[12] Betebenner, D. A.; Degoey, D. A.; Maring, C. J.; Chris Krueger, A.; Iwasaki, N.; Rockway, T. W.; Cooper, C. S.; Anderson, D. D.; Donner, P. L.; Green, B. E.; Kempf, D. J.; Liu, D.; McDaniel, K. F.; Madigan, D.; Motter, C. E.; Pratt, J. K.; Shanley, J. P.; Tufano, M. D.; Wagner, R.; Zhang, R.; Molla, A.; Mo, H.; Pilot-Matias, T.; Masse Sherie, V. L.; Carrick, R. J.; He, W.; Lu, L.; Grampovnik, D. J. WO 2007076034, 2007[Chem. Abstr. 2007, 147, 143454].
[13] Chris Krueger, A.; Madigan, D. L.; Beno, D. W.; Betebenner, D. A.; Carrick, R.; Green, B. E.; He, W.; Liu, D.; Maring, C. J.; McDaniel, K. F.; Mo, H.; Molla, A.; Motter, C. E.; Pilot-Matias, T. J.; Tufano, M. D.; Kempf, D. J. Bioorg. Med. Chem. Lett. 2012, 22, 2212.
[14] Arnold, L. D.; Moyer, M. P.; Sobolov-Jaynes, S. B. US 6395733, 2002[Chem. Abstr. 1997, 126, 144288].
[15] Watanabe, K. A.; Tsann-Long, S. U.; Huang, J. T. WO 9000172, 1990[Chem. Abstr. 1990, 113, 40343].
[16] Ravi Kanth, S.; Venkat Reddy, G.; Hara Kishore, K.; Shanthan Rao, P.; Narsaiah, B.; Surya Narayana Murthy, U. Eur. J. Med. Chem. 2006, 41, 1011.
[17] Naresh Kumar, R.; Jitender Dev, G.; Ravikuma, N.; Krishna Swaroop, D.; Debanjan, B.; Bharath, G.; Narsaiah, B.; Nishant Jain, S.; Gangagni Rao, A. Bioorg. Med. Chem. Lett. 2016, 26, 2927.
[18] Aly, H. M.; Saleh, N. M. Int. J. Adv. Res. 2014, 2, 694.
[19] Song, Z.; Jin, Y.; Ge, Y.; Wang, C.; Zhang, J.; Tang, Z.; Peng, J.; Liu, K.; Li, Y.; Ma, X. Bioorg. Med. Chem. 2016, 24, 5505.
[20] Stuart, G. S.; Guntrip, S. B.; Mckeown, S. C.; Page, M. J.; Smith, K. J.; Vile, S.; Hudson, A. T.; Barraclough, P.; Franzmann, K. W. US 6169091, 2001[Chem. Abstr. 1997, 126, 330623].
[21] Zheng, G. Z.; Mao, Y.; Lee, C. H.; Pratt, J. K.; Koenig, J. R.; Perner, R. J.; Cowart, M. D.; Gfesser, G. A.; McGaraughty, S.; Chu, K. L.; Zhu, C.; Yu, H.; Kohlhaas, K.; Alexander, K. M.; Wismer, C. T.; Mikusa, J.; Jarvis, M. F.; Kowaluk, E. A.; Stewart, A. O. Bioorg. Med. Chem. Lett. 2003, 13, 3041.
[22] Bhagwat, S. S.; Lee, C. H.; Richard, R. J.; Gu, Y. G. WO 0157040, 2001[Chem. Abstr. 2001, 135, 152822].
[23] Al-Ashmawy A. A. K.; Ragab, F. A.; Elokely, K. M.; Anwar, M. M.; Perez-Leal, O.; Rico, M. C.; Gordon, J.; Bichenkov, E.; Mateo, G.; Kassem, E. M. M.; Hegazy, G. H.; Abou-Gharbia, M.; Childers, W. Bioorg. Med. Chem. Lett. 2017, 27, 3117.
[24] Ren, Q.; Wang, T.; Liu, J.; He, H. Chin. J. Org. Chem. 2005, 25, 1530(in Chinese). (任青云, 王涛, 刘建超, 贺红武, 有机化学, 2005, 25, 1530.)
[25] Shamroukh, A. H.; Rashad, A. E.; Abdelmegeid, F. M. J. Chem. Pharm. Res 2016, 8, 734.
[26] Wang, X.; Zeng, Z.; Shi, D.; Tu, S.; Wei, X.; Zong, Z. Chin. J. Org. Chem. 2006, 26, 256(in Chinese). (王香善, 曾兆森, 史达清, 屠树江, 魏贤勇, 宗志敏, 有机化学, 2006, 26, 256.)
[27] Huang, Z.; Liu, X.; Hu, M.; Lin, W.; Shi, D. Chin. J. Org. Chem. 2014, 34, 382(in Chinese). (黄志斌, 刘学成, 胡明华, 林伟, 史达清, 有机化学, 2014, 34, 382.)
[28] Buron, F.; Merour, J. Y.; Akssira, M.; Guillaumet, G.; Routier, S. Eur. J. Med. Chem. 2015, 95, 76.
[29] Deng, L.; Zhong, H.; Wang, S. Chin. J. Org. Chem. 2014, 34, 414(in Chinese). (邓兰青, 钟宏, 王帅, 有机化学, 2014, 34, 414.)
[30] Arikkatt, S. D.; Mathew, B.; Joseph, J.; Chandran, M.; Bhat, A. R.; Krishnakumar, K. Int. J. Org. Bioorg. Chem. 2014, 4, 1.
[31] Rewcastle, G. W.; Palmer, B. D.; Thompson, A. M.; Bridges, A. J.; Cody, D. R.; Zhou, H. R.; Fry, D. W.; McMichael, A.; Denny, W. A. J. Med. Chem. 1996, 39, 1823.
[32] Zhan, D.; Li, S.; Zhao, H.; Lan, M. Chin. J. Org. Chem. 2011, 31, 207(in Chinese). (詹冬梅, 李思远, 赵红莉, 蓝闽波, 有机化学, 2011, 31, 207.)
[33] Yoon, D. S.; Han, Y.; Stark, T. M.; Haber, J. C.; Gregg, B. T.; Stankovich, S. B. Org. Lett. 2004, 6, 4775.
[34] Vercek, B.; Leban, I.; Stanovnik, B.; Tisler, M. J. Org. Chem. 1979, 10, 1695.
[35] Hackler, R. E.; Jourdan, J. P. EP 0414386, 1991[Chem. Abstr. 1991, 115, 71630].
[36] Soloducho, J. Arch. Pharm. 1990, 323, 513.
[37] Shen, Z.; He, X.; Dai, J.; Mo, W.; Hu, B.; Sun, N.; Hu, X. Tetrahedron 2011, 67, 1665.

微波促进的Dimroth重排反应合成吡啶并[2,3-d]嘧啶-4-胺衍生物

Microwave-Accelerated Dimroth Rearrangement for the Synthesis of Pyrido [2, 3-d]pyrimidin-4-amine Derivatives

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