串联氧化碳-氢键氧官能化和噁唑环化构建2-酰基苯并噁唑

doi:10.6023/cjoc202109029

摘要/Abstract

通过铜催化N-(邻羟基苯基)苯乙酰胺的一锅串联亚甲基碳-氢键氧基化以及噁唑环化, 实现了有用的2-酰基苯并噁唑类化合物的合成. 除了具有基于一步多键转化的独特步骤经济性, 以同样原料选择性可控的2-亚甲基苯并噁唑合成以及在合成苯并噻唑方面的扩展应用也是本工作的重要优势.

关键词: 串联, 碳-氢键氧基化, 环化, 2-酰基苯并噁唑, 选择性

The synthesis of useful 2-acyl benzoxazoles has been realized via the tandem methylene C—H oxygenation and oxazole annulation of N-(o-hydroxyphenyl)phenylacetamides via copper catalysis in one-pot fashion. Besides featuring the incomparable step-economy resulting from the multi-step transformation, the tunable synthesis of diverse 2-methylene functionalized benzoxazoles using identical starting materials as well as the expanded synthesis of corresponding benzothiazoles is also attractive advantage of the work.

Key words: tandem, C—H oxygenation, annulation, 2-acyl benzoxazole, selectivity

引用此文

涂志, 赵保丽, 万结平, 王超莉, 刘云云. 串联氧化碳-氢键氧官能化和噁唑环化构建2-酰基苯并噁唑[J]. 有机化学, 2021, 41(12): 4780-4788.

Zhi Tu, Baoli Zhao, Jieping Wan, Chaoli Wang, Yunyun Liu. Aerobic Construction of 2-Acyl Benzoxazole by Tandem C—H Oxygenation and Oxazole Ring Formation[J]. Chinese Journal of Organic Chemistry, 2021, 41(12): 4780-4788.

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Entry	Catalyst	Solvent	Yield/% of 2a	Yield/% of 3a
1	—	AcOH	27	49
2	—	DMSO	0	Trace
3	—	DMF	0	Trace
4	—	EtOH	0	15
5	—	Toluene	0	0
6	CuSO₄	AcOH	45	37
7	Cu(OAc)₂	AcOH	74	11
8	CuI	AcOH	77	Trace
9	CuBr	AcOH	80	Trace
10^c	CuBr	AcOH	69	18
11^d	CuBr	AcOH	78	Trace
12^e	CuBr	AcOH	78	Trace
13^d^,^f	CuBr	AcOH	56	17
14^d^,^g	CuBr	AcOH	75	Trace
15	p-TSA	AcOH	Trace	74
16^h	p-TSA	AcOH	Trace	76
17ⁱ	p-TSA	AcOH	Trace	80
18^j	p-TSA	AcOH	Trace	79
19^d^,^k	CuBr	AcOH	11	59
20^d^,^l	CuBr	AcOH	77	Trace

Entry	Catalyst	Solvent	Yield/% of 2a	Yield/% of 3a
1	—	AcOH	27	49
2	—	DMSO	0	Trace
3	—	DMF	0	Trace
4	—	EtOH	0	15
5	—	Toluene	0	0
6	CuSO₄	AcOH	45	37
7	Cu(OAc)₂	AcOH	74	11
8	CuI	AcOH	77	Trace
9	CuBr	AcOH	80	Trace
10^c	CuBr	AcOH	69	18
11^d	CuBr	AcOH	78	Trace
12^e	CuBr	AcOH	78	Trace
13^d^,^f	CuBr	AcOH	56	17
14^d^,^g	CuBr	AcOH	75	Trace
15	p-TSA	AcOH	Trace	74
16^h	p-TSA	AcOH	Trace	76
17ⁱ	p-TSA	AcOH	Trace	80
18^j	p-TSA	AcOH	Trace	79
19^d^,^k	CuBr	AcOH	11	59
20^d^,^l	CuBr	AcOH	77	Trace