Iodine-Dimethyl sulfoxide Promoted Synthesis of Novel TetracyclicThiazolo[3',2':2,3]pyrido[4,5-d]pyrido[1,2-a]pyrimidinones

doi:10.6023/cjoc201904033

Chinese Journal of Organic Chemistry ›› 2019, Vol. 39 ›› Issue (10): 2808-2812.DOI: 10.6023/cjoc201904033 Previous Articles Next Articles

Special Issue: 元素有机化学合辑2018-2019

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碘-二甲基亚砜促进新型四环噻唑并[3',2':2,3]吡啶并[4,5-d]吡啶并[1,2-a]嘧啶酮类衍生物的合成

徐姣^a^b, 张丽宏^b, 张美琦^b, 刘秀波^b, 马伟^a^b^*(), 唐益鑫^c, 王道林^c^*()

^a 东北林业大学林木遗传育种国家重点实验室哈尔滨 150040
^b 黑龙江中医药大学药学院哈尔滨 150040
^c 渤海大学化学化工学院锦州 121003

收稿日期:2019-04-12 修回日期:2019-05-26 发布日期:2019-06-12
通讯作者: 马伟,王道林 E-mail:mawei@hljucm.net;wangdaolin@sina.com

Iodine-Dimethyl sulfoxide Promoted Synthesis of Novel TetracyclicThiazolo[3',2':2,3]pyrido[4,5-d]pyrido[1,2-a]pyrimidinones

Xu Jiao^a^b, Zhang Lihong^b, Zhang Meiqi^b, Liu Xiubo^b, Ma Wei^a^b^*(), Tang Yixin^c, Wang Daolin^c^*()

^a State Key Laboratory of Tree Genetics and Breeding, Northeast Forestry University, Harbin 150040
^b College of Pharmacy, Heilongjiang University of Chinese Medicine, Harbin 150040
^c College of Chemistry and Chemical Engineering, Bohai University, Jinzhou 121003

Received:2019-04-12 Revised:2019-05-26 Published:2019-06-12
Contact: Ma Wei,Wang Daolin E-mail:mawei@hljucm.net;wangdaolin@sina.com

An iodine-dimethyl sulfoxide (I₂-DMSO) promoted efficient method is described for the synthesis of thiazolo- [3',2':2,3]pyrido[4,5-d]pyrido[1,2-a]pyrimidin-5-ones (5) via Pictet-Spengler cyclization. The key intermediate, 2-(3-amino- 5-phenylaminothiazolo-2-yl)-4H-pyrido[1,2-a]pyrimidin-4-one (3), was readily prepared from 2-chloromethyl-4H-pyrido- [1,2-a]pyrimidin-4-one (1) and potassium N-phenyl-N'-cyano-imido-thiocarbonate (2) by Thorpe-Ziegler isomerization. The novel synthetic method offers the advantage of mild reaction conditions, operational simplicity and higher yields.

Key words: pyrido[1,2-a]pyrimidine, thiazolopyridine, Thorpe-Ziegler isomerization, Pictet-Spengler reaction, I₂-DMSO

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Xu Jiao, Zhang Lihong, Zhang Meiqi, Liu Xiubo, Ma Wei, Tang Yixin, Wang Daolin. Iodine-Dimethyl sulfoxide Promoted Synthesis of Novel TetracyclicThiazolo[3',2':2,3]pyrido[4,5-d]pyrido[1,2-a]pyrimidinones[J]. Chinese Journal of Organic Chemistry, 2019, 39(10): 2808-2812.

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References 16

[1]	(a) Miller, C. M.; McCarthy, F.O. RSC Adv. 2012, 2, 8883. doi: 10.1039/c2ra20584j
	(b) Izuhra, D.; Swager, T.M. J. Am. Chem. Soc. 2009, 131, 17724. doi: 10.1039/c2ra20584j
	(c) Palmer, A. M.; Grobbel, B.; Jecke, C.; Brehm, C.; Zimmermann, P. J.; Buhr, W.; Feth, M.P.; Simon, W. A.; Kromer, W. J. Med. Chem. 2007,50, 6240. doi: 10.1039/c2ra20584j
[2]	Swinbourne, F. J.; Hunt, J. H.; Klinkert, G. Adv. Heterocycl. Chem. 1979, 23, 103.
[3]	Smith, R. L.; Barrett, R. J.; Sanders-Bush, E. J. Pharmacol. Exp. Ther. 1995, 275, 1050.
[4]	Hermecz, I.; Mészáros, Z. Med. Res. Rev. 1988, 8, 203.
[5]	Colpaert, F.C. Nat. Rev. Drug Discovery 2003, 2, 315.
[6]	Donghi, M.; Kinzel, O. D.; Summa, V . Bioorg. Med. Chem. Lett. 2009, 19, 1930. doi: 10.1016/j.bmcl.2009.02.055
[7]	(a) Katritzky, A. R.; Rogers, J. W.; Witek, R. M.; Nair, S. K. ARKIVOC 2004, viii, 52.
	(b) Knight, Z. A.; Chiang, G. G.; Alaimo, P. J.; Kenski, D. M.; Ho, C. B.; Coan, K.; Abraham, R. T.; Shokat, K.M. Bioorg. Med. Chem. 2004, 12, 4749.
[8]	Awouters, F.; Vermeire, J.; Smeyers, F.; Vermote, P.; Van Beek, R.; Niemegeers, C.J. E. Drug Dev. Res. 1986, 8, 95.
[9]	Kapui, Z.; Varga, M.; Urban-Szabo, K.; Mikus, E.; Szabo, T.; Szeredi, J.; Batori, S.; Finance, O.; Armani, P. J. Pharmacol. Exper. Ther. 2003, 305, 451.
[10]	(a) Chen, Z. W.; Wen, Y. L.; Ding, H.; Luo, G. T.; Ye, M.; Liu, L. X.; Xue, J. Tetrahedron Lett. 2017, 58, 13. doi: 10.1016/j.tetlet.2016.11.079
	(b) Lee, H. J.; Song, Y.H. Heterocycl. Commun. 2016, 22, 59. doi: 10.1016/j.tetlet.2016.11.079
	(c) Guchhait, S.; Priyadarshani, G. J. Org. Chem. 2015, 80, 8482. doi: 10.1016/j.tetlet.2016.11.079
	(d) Del Turco, S.; Sartini, S.; Sentieri, C.; Saponaro, C.; Navarra, T.; Dario, B.; Settimo, F. D.; Motta, C. L.; Basta, G. Eur. J. Med. Chem. 2014, 72, 102. doi: 10.1016/j.tetlet.2016.11.079
	(e) Djekou, S.; Gellis, A.; Maldonado, J.; Crozet, M.P.; Vanelle, P. Heterocycles. 2000, 55, 535. doi: 10.1016/j.tetlet.2016.11.079
[11]	(a) Togo, H.; Iida, S. Synlett 2006,2159.
	(b) Shen, S. S.; Xu, X. P.; Ji, S.J. Chin. J. Org. Chem. 2009, 29, 806 (in Chinese).
	( 沈舒苏, 徐小平, 纪顺俊, 有机化学, 2009, 29, 806.)
	(c) Jereb, M.; VraziC, D.; Zupan, M. Tetrahedron 2011, 67, 1355.
	(d) Parvatkar, P. T.; Parameswaran, P. S.; Tilve, S.G. Chem.-Eur. J. 2012, 18, 5460.
[12]	(a) Yin, G.; Fan, L.; Ren, T.; Zheng, C.; Tao, Q.; Wu, A She, N. Org. Biomol. Chem. 2012, 10, 8877.
	(b) Ahmed, N.; Babu, B.V. Synth. Commun. 2013, 43, 3044.
	(c) Wu, X.; Gao, Q.; Liu, S.; Wu, A. Org. Lett. 2014, 16, 2888
	(d) Hu, F.; Gao, W. C.; Chang, H. H.; Li, X.; Wei, W.L. Chin. J. Org. Chem. 2015, 35, 1848
	( 胡飞, 高文超, 常宏宏, 李兴, 魏文珑, 有机化学, 2015, 35, 1848.)
	(e) Wang, D. Y.; Zhang, R. X.; Lin, S.; Deng, R. H.; Yan, Z.H. Chin. J. Org. Chem. 2016, 36, 2757(in Chinese).
	( 王丁意, 张荣兴, 林森, 邓瑞红, 严兆华, 有机化学, 2016, 36, 2757.)
	(f) Wang, Y. F.; Yang, Y. J.; Huang, L.; Jie, K.; Guo, S. M.; Cai, H. Chin. J. Org. Chem. 2017, 37, 3220(in Chinese).
	( 王玉凤, 杨雅杰, 黄玲, 揭坤, 郭生梅, 蔡琥, 有机化学, 2017, 37, 3220.)
[13]	(a) Tang, Y. X.; Wang, D. L.; Qiang, J. H. Heterocycles 2017, 94, 1351. doi: 10.3987/COM-17-13734
	(b) Wang, D. L.; Wang, D.; Yan, L.; Pan, G. Y.; Yang, J. N. Heterocycles 2016, 92, 552. doi: 10.3987/COM-17-13734
	(c) Wang, D. L.; Wang, D.; Yan, L.; Pan, G. Y.; Yang, J.N. Chin. Chem. Lett. 2016, 27, 953. doi: 10.3987/COM-17-13734
	(d) Wang, D. L.; Zhou, T.; Xing, J. J.; Qiang, J. H.; Liu, L. Heterocycles 2016, 92, 733. doi: 10.3987/COM-17-13734
[14]	(a) Gefenas, V.; Stankevičūte, Ž.; Malinauskas, A. Chem. Heterocycl. Compd. 2010, 46, 372.
	(b) Shestopalov, A. M.; Fedorov, A. E.; Belyakov, P.A. Chem. Heterocycl. Compd. 2000, 36, 609.
[15]	Böhme, H.; Weisel, K.H. Arch. Pharm. 1977, 310, 26.
[16]	Fromm, E. Ber. Dtsch. Chem. Ges. 1922, 55, 804.

碘-二甲基亚砜促进新型四环噻唑并[3',2':2,3]吡啶并[4,5-d]吡啶并[1,2-a]嘧啶酮类衍生物的合成

Iodine-Dimethyl sulfoxide Promoted Synthesis of Novel TetracyclicThiazolo[3',2':2,3]pyrido[4,5-d]pyrido[1,2-a]pyrimidinones

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Entry	Catalyst (mol%)	Solvent	Temp./℃	Time/h	Yield/%
1	I₂ (10)	DMSO	80	11	67
2	I₂ (20)	DMSO	80	9	78
3	I₂ (30)	DMSO	80	8	76
4	I₂ (20)	DMSO	90	9	86
5	I₂ (20)	DMSO	100	8	82
6	I₂(20)	HOAc	90	8	73
7	I₂ (20)	DMF	90	12	77
8	I₂ (20)	MeCN	90	15	52
9	SA (20)	DMSO	90	10	70
10	TFA (20)	DMSO	90	8	74
11	p-TsOH (20)	DMSO	90	8	75

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