Electrocatalysis Decarboxylative Annulation of Benzol[e][1,2,3]-oxathiazine-2,2-dioxides with N-Arylglycines

doi:10.6023/cjoc202310027

Abstract

Benzo[e]imidazo[1,2,3]oxathiazine-5,5-dioxides are a significant class of fused N-heterocycles, possessing diverse biological and pharmacological activities. In this paper, a novel method for the synthesis of benzo[e]imidazo[1,2,3]oxathia- zine-5,5-dioxides through electrochemical cascade decarboxylative coupling/annulation of benzol[e][1,2,3]oxathiazine- 2,2-dioxides with N-arylglycines was reported. A wide variety of benzo[e]imidazo[1,2,3]oxathiazine-5,5-dioxides were efficiently constructed in good to excellent yields. This strategy offers notable benefits, such as gentle and environmentally friendly conditions, operational simplicity, impressive yields, excellent tolerance towards various functional groups, and straightforward scalability, making it highly valuable for practical applications.

Key words: organic electrochemical synthesis, cascade reaction, decarboxylative coupling, annulation reaction, N‑arylgly- cines

Cite this article

Linheng He, Wen Xia, Yuxiang Zhou, Xianyong Yu. Electrocatalysis Decarboxylative Annulation of Benzol[e][1,2,3]-oxathiazine-2,2-dioxides with N-Arylglycines[J]. Chinese Journal of Organic Chemistry, 2024, 44(3): 997-1004.

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Entry	Variation from “standard conditions”	Yield^b/%
1	None	95
2	Pt(＋)\|C(－) instead of Pt(＋)\|Pt(－)	77
3	C(＋)\|Pt(－) instead of Pt(+)\|Pt(－)	74
4	C(＋)\|C(－) instead of Pt(+)\|Pt(－)	38
5	Et₄NClO₄ instead of Et₄NBF₄	78
6	Et₄NPF₆ instead of Et₄NBF₄	83
7	Et₄NI instead of Et₄NBF₄	87
8	LiBF₄ instead of Et₄NBF₄	81
9	MeCN instead of EtOH	77
10	DMSO instead of EtOH	43
11	DMF instead of EtOH	39
12	Without Et₄NBF₄	N.R.
13	without electrical current	N.R.

Entry	Variation from “standard conditions”	Yield^b/%
1	None	95
2	Pt(＋)\|C(－) instead of Pt(＋)\|Pt(－)	77
3	C(＋)\|Pt(－) instead of Pt(+)\|Pt(－)	74
4	C(＋)\|C(－) instead of Pt(+)\|Pt(－)	38
5	Et₄NClO₄ instead of Et₄NBF₄	78
6	Et₄NPF₆ instead of Et₄NBF₄	83
7	Et₄NI instead of Et₄NBF₄	87
8	LiBF₄ instead of Et₄NBF₄	81
9	MeCN instead of EtOH	77
10	DMSO instead of EtOH	43
11	DMF instead of EtOH	39
12	Without Et₄NBF₄	N.R.
13	without electrical current	N.R.

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电催化N-芳基甘氨酸和苯并[e][1,2,3]噁噻嗪-2,2-二氧化物的串联脱羧环化反应