Synthesis of dihydrocarbazoles via (4+2) annulation of donor-acceptor cyclopropanes to indoles

doi:10.1016/j.tet.2015.12.023

	Synthesis of dihydrocarbazoles via (4+2) annulation of donor-acceptor cyclopropanes to indoles
Department	OSSO国家重点实验室
	Liu, Changhui 1; Zhou, Li 1; Huang, Wenbo 1; Wang, Man 1; Gu YL(顾彦龙)1,2; Gu YL(顾彦龙)
	2016
Source Publication	Tetrahedron
ISSN	0040-4020
Volume	72 Issue:4 Pages:563-570
Abstract	Dihydrocarbazoles were synthesized through a novel [4+2] annulation of donor-acceptor cyclopropanes (DACs) to indoles. This reaction was performed in ethanol by using para-toluenesulfonic acid as catalyst. Mechanism of this reaction might involve the following three steps: (i) an electrophilic ring-opening reaction of the DACs with indoles, in which C3 position of indole acts as a nucleophilic site, (ii) an intramolecular dehydration induced ring-closing reaction occurs that offers a spiro intermediate, and (iii) a following 1,2-migration which leading to a dihydrocarbazole scaffold. Otherwise, dihydroisoindole can also be constructed by replacing the indole component with pyrrole as nucleophile.
Keyword	Dihydrocarbazoles Cyclopropanes Acid Catalysis Ring-opening Reactions
Subject Area	物理化学与绿色催化
DOI	10.1016/j.tet.2015.12.023
Funding Organization	National Natural Science Foundation of China (21173089;21373093);Chutian Scholar Program of the Hubei Provincial Government and the Cooperative Innovation Center of Hubei Province;the fundamental research funds for the central universities in China (2014ZZGH019)
Indexed By	SCI
If	2.651
Language	英语
compositor	第二作者单位
Citation statistics	Cited Times:24[WOS] [WOS Record] [Related Records in WOS]
Document Type	期刊论文
Identifier	http://ir.licp.cn/handle/362003/19701
Collection	羰基合成与选择氧化国家重点实验室（OSSO）
Corresponding Author	Gu YL(顾彦龙)
Affiliation	1.Huazhong Univ Sci & Technol, Key Lab Mat Chem & Serv Failure, Key Lab Mat Chem Energy Convers & Storage, Minist Educ,Sch Chem & Chem Engn, Wuhan 430074, Peoples R China 2.Chinese Acad Sci, Lanzhou Inst Chem Phys, State Key Lab Oxo Synth & Select Oxidat, Lanzhou 730000, Peoples R China
Recommended Citation GB/T 7714	Liu, Changhui,Zhou, Li,Huang, Wenbo,et al. Synthesis of dihydrocarbazoles via (4+2) annulation of donor-acceptor cyclopropanes to indoles[J]. Tetrahedron,2016,72(4):563-570.
APA	Liu, Changhui,Zhou, Li,Huang, Wenbo,Wang, Man,Gu YL,&顾彦龙.(2016).Synthesis of dihydrocarbazoles via (4+2) annulation of donor-acceptor cyclopropanes to indoles.Tetrahedron,72(4),563-570.
MLA	Liu, Changhui,et al."Synthesis of dihydrocarbazoles via (4+2) annulation of donor-acceptor cyclopropanes to indoles".Tetrahedron 72.4(2016):563-570.

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