Stereoselective synthesis of sulfonated 1-indenones via radical-triggered multi-component cyclization of β-alkynyl propenones

被引：113

作者：

Shen, Zheng-Jia ^{[1
]}

Wu, Ya-Nan ^{[1
]}

He, Chun-Lan ^{[1
]}

He, Long ^{[1
]}

Hao, Wen-Juan ^{[1
]}

Wang, Ai-Fang ^{[1
]}

Tu, Shu-Jiang ^{[1
]}

Jiang, Bo ^{[1
]}

机构：

[1] Jiangsu Normal Univ, Sch Chem & Mat Sci, Xuzhou 221116, Peoples R China

来源：

CHEMICAL COMMUNICATIONS | 2018年 / 54卷 / 05期

关键词：

MEOTF-INDUCED CARBOANNULATION; AQUILINUM-VAR-LATIUSCULUM; SULFUR-DIOXIDE; INTERNAL ALKYNES; C-H; ACETYLCHOLINESTERASE INHIBITORS; CARBONYLATIVE CYCLIZATION; CATALYZED ANNULATION; RECEPTOR ANTAGONISTS; CASCADE CYCLIZATION;

D O I：

10.1039/c7cc08516h

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

New radical-triggered multi-component cyclizations of beta-alkynyl propenones have been developed, leading to 50 examples of sulfonated 1-indenones with generally good yields and high levels of stereoselectivity. The oxidant-free azosulfonylation of beta-alkynyl propenones with aryldiazonium salts and DABSO was realized under the neutral-redox conditions where TBHP enabled the direct selenosulfonylation of b-alkynyl propenones by combining sulfinic acids and diphenyl diselenide. This protocol features a broad substrate scope, high functional group tolerance and mild reaction conditions.

引用

页码：445 / 448

页数：4

共 70 条

[1] 2-ARYLINDENES AND 2-ARYLINDENONES - SYNTHESIS OF PROBES TO STUDY THE BINDING ORIENTATION OF UNSYMMETRICAL NONSTEROIDAL LIGANDS TO THE ESTROGEN-RECEPTOR [J].

ANSTEAD, GM ;

ENSIGN, JL ;

PETERSON, CS ;

KATZENELLENBOGEN, JA .

JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (07) :1485-1491

[2]

BACKVALL JE, 1993, J ORG CHEM, V58, P5221

[3] Synthesis of some imidazolyl-substituted 2-benzylidene indanone derivatives as potent aromatase inhibitors for breast cancer therapy [J].

Bansal, Ranju ;

Narang, Gaurav ;

Zimmer, Christina ;

Hartmann, Rolf W. .

MEDICINAL CHEMISTRY RESEARCH, 2011, 20 (06) :661-669

[4] FULVENES AND THERMOCHROMIC ETHYLENES .30. EXPERIMENTS IN THE 2,3-DIARYLINDONE SERIES [J].

BERGMANN, ED .

JOURNAL OF ORGANIC CHEMISTRY, 1956, 21 (04) :461-464

[5] RADICAL CYCLIZATION OF DIENES AND ENYNES USING TOLSO2SEPH [J].

BRUMWELL, JE ;

SIMPKINS, NS ;

TERRETT, NK .

TETRAHEDRON LETTERS, 1993, 34 (07) :1219-1222

[6]

BRUMWELL JE, 1994, TETRAHEDRON, V50, P13533

[7] Further studies on imidazo[4,5-b] pyridine AT1 angiotensin II receptor antagonists.: Effects of the transformation of the 4-phenylquinoline backbone into 4-phenylisoquinolinone or 1-phenylindene scaffolds [J].

Cappelli, Andrea ;

Mohr, Gal. la Pericot ;

Giuliani, Germano ;

Galeazzi, Simone ;

Anzini, Maurizio ;

Mennuni, Laura ;

Ferrari, Flora ;

Makovec, Francesco ;

Kleinrath, Eva M. ;

Langer, Thierry ;

Valoti, Massimo ;

Giorgi, Gianluca ;

Vomero, Salvatore .

JOURNAL OF MEDICINAL CHEMISTRY, 2006, 49 (22) :6451-6464

[8] Anticancer activity, toxicity and pharmacokinetic profile of an indanone derivative [J].

Chanda, Debabrata ;

Bhushan, Shashi ;

Guru, Santosh K. ;

Shanker, Karuna ;

Wani, Z. A. ;

Rah, B. A. ;

Luqman, Suaib ;

Mondhe, Dilip M. ;

Pal, Anirban ;

Negi, Arvind S. .

EUROPEAN JOURNAL OF PHARMACEUTICAL SCIENCES, 2012, 47 (05) :988-995

[9] Exploration of Visible-Light Photocatalysis in Heterocycle Synthesis and Functionalization: Reaction Design and Beyond [J].

Chen, Jia-Rong ;

Hu, Xiao-Qiang ;

Lu, Liang-Qiu ;

Xiao, Wen-Jing .

ACCOUNTS OF CHEMICAL RESEARCH, 2016, 49 (09) :1911-1923

[10] Rhodium-Catalyzed Direct Annulation of Aldehydes with Alkynes Leading to Indenones: Proceeding through in Situ Directing Group Formation and Removal [J].

Chen, Shuyou ;

Yu, Jintao ;

Jiang, Yan ;

Chen, Fan ;

Cheng, Jiang .

ORGANIC LETTERS, 2013, 15 (18) :4754-4757

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