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

doi:10.6023/cjoc201904033

有机化学 ›› 2019, Vol. 39 ›› Issue (10): 2808-2812.DOI: 10.6023/cjoc201904033 上一篇下一篇

所属专题：元素有机化学合辑2018-2019

研究论文

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

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摘要/Abstract

介绍了在碘-二甲基亚砜(I₂-DMSO)促进作用下, 通过Pictet-Spengler反应合成噻唑并[3',2':2,3]吡啶并[4,5-d]吡啶并[1,2-a]嘧啶酮(5)衍生物的合成方法. 该反应的关键中间体2-(3-氨基-5-苯氨基噻唑-2-基)-4H-吡啶[1,2-a]嘧啶-4-酮(3), 由2-氯甲基-4H-吡啶[1,2-a]嘧啶-4-酮(1)与N-苯基-N'-氰基-咪唑硫代碳酸钾(2)通过Thorpe-Ziegler异构化反应制得. 该合成方法反应条件温和, 操作简单, 收率高.

关键词: 吡啶[1,2-a]嘧啶, 噻唑并吡啶, Thorpe-Ziegler异构化, Pictet-Spengler反应, I₂-DMSO

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

引用此文

徐姣, 张丽宏, 张美琦, 刘秀波, 马伟, 唐益鑫, 王道林. 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[J]. 有机化学, 2019, 39(10): 2808-2812.

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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图/表 3

Scheme 1. Syntheses of thiazolopyrido-fused pyridopyrimidines 5a R=Ph, 5b R=4-MeC6H4, 5c R=2-MeOC6H4, 5d R=4-MeOC6H4, 5e R=3,4-(MeO)2C6H3, 5f R=4-HOC6H4, 5g R=2-FC6H4, 5h R= 4-FC6H4, 5i R=4-ClC6H4, 5j R=4-NO2C6H4, 5k R=2-furyl, 5l R= 2-thienyl

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

Table 1. Optimization of reaction conditions on the synthesis of 5aa

Scheme 2. Proposed reaction mechanism for the formation of compound 5

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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

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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