Metal-Free Rapid Synthesis of 2-Aroylamino Naphtho[1, 2-d]thiazoles

doi:10.6023/cjoc201904029

Chinese Journal of Organic Chemistry ›› 2019, Vol. 39 ›› Issue (11): 3199-3206.DOI: 10.6023/cjoc201904029 Previous Articles Next Articles

无金属催化快速合成2-芳酰氨基萘并[1, 2-d]噻唑

刘天宝*(), 彭艳芬, 桂美芳, 章敏*()

池州学院化学与材料工程学院微纳粉体与先进能源材料安徽普通高校重点实验室安徽池州 247000

收稿日期:2019-04-11 发布日期:2019-07-03
通讯作者: 刘天宝,章敏 E-mail:tianbaoliu1979@126.com;287323206@qq.com
基金资助:
国家自然科学基金(21271035);安徽省自然科学基金(1808085QB48);安徽省有机化学省级教学团队(2017jxtd051)

Metal-Free Rapid Synthesis of 2-Aroylamino Naphtho[1, 2-d]thiazoles

Liu Tianbao*(), Peng Yanfen, Gui Meifang, Zhang Min*()

Key Laboratory of Micro-nano Powder and Advanced Energy Materials of Anhui Higher Education Institutes, Department of Chemical and Material Engineering, Chizhou University, Chizhou, Anhui 247000

Received:2019-04-11 Published:2019-07-03
Contact: Liu Tianbao,Zhang Min E-mail:tianbaoliu1979@126.com;287323206@qq.com
Supported by:
the National Natural Science Foundation of China(21271035);the Natural Science Foundation of Anhui Province(1808085QB48);the Provincial Teaching Team of Organic Chemistry(2017jxtd051)

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Abstract

A novel and efficient approach has been developed to synthesize 2-aroylamino naphtho[1, 2-d]thiazole compounds through the reaction between 3-[1-(4-substituted naphthyl)]-1-aroylthiourea and iodosobenzene diacetate (IBD) under ambient air. A library of naphtho[1, 2-d]thiazole derivatives having a variety of substituents has been synthesized. A plausible reaction pathway has been predicted. This reaction offers a metal-free synthesis, broad substrate scope, easily accessible reactants, excellent regioselectivity, room temperature reaction conditions under ambient air. The reported method is the efficient approach for the synthesis of naphtho[1, 2-d]thiazole derivatives.

Key words: naphtho[1, 2-d]thiazole, thiourea, iodosobenzene diacetate, metal-free

Cite this article

Liu Tianbao, Peng Yanfen, Gui Meifang, Zhang Min. Metal-Free Rapid Synthesis of 2-Aroylamino Naphtho[1, 2-d]thiazoles[J]. Chinese Journal of Organic Chemistry, 2019, 39(11): 3199-3206.

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References 12

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无金属催化快速合成2-芳酰氨基萘并[1, 2-d]噻唑

Metal-Free Rapid Synthesis of 2-Aroylamino Naphtho[1, 2-d]thiazoles

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Entry	IBD/equiv.	Temp./℃	Time/min	Solvent	Yield^b/%
1	1.0	80	30	CH₃CN	68
2	1.1	80	30	CH₃CN	74
3	1.2	80	30	CH₃CN	83
4	1.3	80	30	CH₃CN	75
5	1.4	80	30	CH₃CN	67
6	1.2	70	30	CH₃CN	83
7	1.2	60	30	CH₃CN	82
8	1.2	50	30	CH₃CN	86
9	1.2	40	30	CH₃CN	85
10	1.2	30	30	CH₃CN	86
11	1.2	20	30	CH₃CN	86
12	1.2	14	30	CH₃CN	44
13	1.2	20	30	CH₃CH₂OH	60
14	1.2	20	30	CH₃OH	65
15	1.2	20	30	THF	43
16	1.2	20	30	Petroleum ether	22
17	1.2	20	30	1, 4-Dioxane	40
18	1.2	20	30	AcOH	80
19	1.2	20	20	CH₃CN	86
20	1.2	20	10	CH₃CN	86
21	1.2	20	5	CH₃CN	87