NaNO2-catalyzed reaction of cyclohexenone-MBH acetates: A convenient synthesis of 2-methylene-3-cyclohexenones

被引：5

作者：

Jiang, Lin ^{[1
]}

Li, Lu ^{[1
]}

Li, Min ^{[1
]}

Yuan, Ming-Wei ^{[1
]}

Yuan, Ming-Long ^{[1
]}

机构：

[1] Yunnan Minzu Univ, Natl & Local Joint Engn Res Ctr Green Preparat Tec, Sch Chem & Environm, Kunming, Peoples R China

来源：

SYNTHETIC COMMUNICATIONS | 2023年 / 53卷 / 18期

基金：

中国国家自然科学基金;

关键词：

Cyclohexenone-MBH acetate; sodium nitrite; 2-methylene-3-cyclohexenone; transition metal-free catalysis; synthesis; CATALYZED 5+1 CYCLOADDITION; BAYLIS-HILLMAN ACETATES; ADDUCTS; ALDEHYDES; EFFICIENT;

D O I：

10.1080/00397911.2023.2235625

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient NaNO2-catalyzed synthesis of 2-methylene-3-cyclohexenones from easily accessible cyclohexenone-MBH acetates has been established for the first time. Target products were rapidly generated in moderate to high yields and with relatively high E/Z selectivity. Easy operation, good functional group tolerance, mild reaction conditions and the practicality of high efficiency of NaNO2 for the formation of 2-methylene-3-cyclohexenones constitute the attractive advantages of this reaction.

引用

页码：1520 / 1528

页数：9

共 23 条

[1] Synthetic studies on N-methylwelwitindolinone C isothiocyanate (welwistatin) and related substructures [J].

Avendaño, C ;

Menéndez, JC .

CURRENT ORGANIC SYNTHESIS, 2004, 1 (01) :65-82

[2] The first diastereoselective synthesis of cinerins A-C, PAF-antagonistic macrophyllin-type bicyclo[3.2.1]octane neolignans, using a novel Pd-catalysed oxyarylation [J].

Coy B, Ericsson D. ;

Cuca S, Luis E. ;

Sefkow, Michael .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2010, 8 (09) :2003-2005

[3] A multicomponent approach to substituted benzenes involving sequential nickel-catalyzed reactions [J].

ElDouhaibi, Ahmad Samih ;

Lozanov, Mario ;

Montgomery, John .

TETRAHEDRON, 2006, 62 (49) :11460-11469

[4] Dimethyl sulfide-boron trihalide-mediated reactions of α,β-unsaturated ketones with aldehydes:: one-pot synthesis of Baylis-Hilman adducts and α-halomethyl enones [J].

Iwamura, T ;

Fujita, M ;

Kawakita, T ;

Kinoshita, S ;

Watanabe, S ;

Kataoka, T .

TETRAHEDRON, 2001, 57 (40) :8455-8462

[5] The dipolar route to naphtho[2,1-c]isoxazoles from the Baylis-Hillman adducts of 2-alkynylbenzaldehydes [J].

Ji, Sang-Hoon ;

Hong, Wan Pyo ;

Ko, Seung Ho ;

Lee, Kee-Jung .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 2006, 43 (03) :799-801

[6] Regio- and diastereoselective synthesis of 3,4-dihydro-2H-benzo [4,5] imidazo[2,1-b] [1,3]thiazine derivatives via DBU-catalyzed [3+3] annulation of MBH carbonates with 2-mercaptobenzimidazoles [J].

Jiang, Lin ;

Peng, Peiying ;

Yu, Liudong ;

Jiang, Dengbang ;

Wang, Yidan ;

Li, Hongli ;

Yuan, Minglong ;

Yuan, Mingwei .

TETRAHEDRON, 2021, 98

[7] Stereoselective allylic 1,3-dienylation of Morita-Baylis-Hillman carbonates via an alkylation-denitration sequence [J].

Jiang, Lin ;

Yu, Liu-Dong ;

Peng, Pei-Ying ;

Li, Hong-Li ;

Jiang, Deng-Bang ;

Wang, Yi-Dan ;

Yuan, Ming-Long ;

Yuan, Ming-Wei .

SYNTHETIC COMMUNICATIONS, 2021, 51 (03) :419-427

[8] Rh-catalysed [5+1] cycloaddition of allenylcyclopropanes and CO: reaction development and application to the formal synthesis of (-)-galanthamine [J].

Liu, Cheng-Hang ;

Yu, Zhi-Xiang .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2016, 14 (25) :5945-5950

[9] Efficient and Stereoselective Rearrangement of Baylis-Hillman Acetates Catalyzed by Gold(I) Chloride/Silver(I) Trifluoromethanesulfonate [J].

Liu, Yunkui ;

Mao, Dajie ;

Qian, Jianqiang ;

Lou, Shaojie ;

Xu, Zhenyuan ;

Zhang, Yongmin .

SYNTHESIS-STUTTGART, 2009, (07) :1170-1174

[10] STRUCTURE-ACTIVITY-RELATIONSHIPS OF ILLUDINS - ANALOGS WITH IMPROVED THERAPEUTIC INDEX [J].

MCMORRIS, TC ;

KELNER, MJ ;

WANG, W ;

ESTES, LA ;

MONTOYA, MA ;

TAETLE, R .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (25) :6876-6883

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