“One-pot” Synthesis of 1-Vinyl-2-pyrrolidone with Protic Functional Groups in 3-Position

2009 ◽  
Vol 210 (22) ◽  
pp. 1973-1978 ◽  
Author(s):  
Mónica Pérez Perrino ◽  
Rodrigo Navarro ◽  
Myriam Gómez Tardajos ◽  
Alberto Gallardo ◽  
Helmut Reinecke
Synlett ◽  
2020 ◽  
Vol 31 (14) ◽  
pp. 1430-1434
Author(s):  
Ming Bian ◽  
Jin-feng Zhou ◽  
Dong-min Tang

An efficient and practical protocol for the geminal heterodihalogenation of methyl ketones by using readily available dimethyl sulfoxide and a combination of HCl and HBr is reported. Control experiments suggested that the acidity of the solution, as well as the oxidizing ability and nucleophilicity of the dimethyl sulfoxide might work cooperatively in ensuring the success of the tandem substitution. Its operational simplicity, easy accessibility, and mild oxidative conditions suggest that the present strategy might be useful for the assembly of bromochloromethyl functional groups in drug discovery.


2008 ◽  
Vol 63 (7) ◽  
pp. 865-870 ◽  
Author(s):  
Chunxiang Kuang ◽  
Yubo Jiang ◽  
Qing Yang ◽  
Wensheng Zhang ◽  
Yaolin Wen

A facile one-pot synthesis of functionalized (E)-β -arylvinyl bromides bearing various 4-alkoxycarbonyl and 4-aryloxycarbonyl groups was achieved by debrominative decarboxylation of anti-2,3- dibromo-3-(4-carboxyphenyl)propanoic acid in the presence of AgOAc and subsequent esterification in the presence of dicyclohexyl carbodiimide and dimethylaminopyridine. This method gives (E)-β - arylvinyl bromides in high stereoselectivities and high yields, and tolerates aldehyde, ester, and nitro functional groups.


Heterocycles ◽  
1992 ◽  
Vol 34 (3) ◽  
pp. 429 ◽  
Author(s):  
Hidetsugu Wakabayashi ◽  
Paw-Wang Yang ◽  
Chi-Phi Wu ◽  
Kimio Shindo ◽  
Sumio Ishikawa ◽  
...  

RSC Advances ◽  
2016 ◽  
Vol 6 (23) ◽  
pp. 19571-19575 ◽  
Author(s):  
Jun Ge ◽  
Xiaojian Wang ◽  
Tianqi Liu ◽  
Zeyu Shi ◽  
Qiong Xiao ◽  
...  

A practical method for one-pot synthesis of substituted phenanthridines is described. Via this method, a series of substituted phenanthridines are obtained in good yields with remarkable functional groups compatibility.


Synlett ◽  
2019 ◽  
Vol 30 (05) ◽  
pp. 615-619 ◽  
Author(s):  
Ji-Yu Wang ◽  
Xu-Ling Chen ◽  
Yu Dong ◽  
Shuai He ◽  
Rui Zhang ◽  
...  

A one-pot synthesis of 2-(N-substituted amino)-1,4-naphthoquinones from 1,4-naphthoquinones and nitro compounds in water has been developed. This method features mild reaction conditions and provides aromatic nitro compounds with various functional groups such as halogens, methylthio, ester, amide, even allyl, propargyl, and heterocycles, as well as aliphatic nitro compounds that are well tolerated. This method can be scaled up and we conducted further transformation of the obtained 2-(N-substituted amino)-1,4-naphthoquinones to synthesize carbazolequinone derivatives.


Catalysts ◽  
2020 ◽  
Vol 10 (11) ◽  
pp. 1348
Author(s):  
Sergey A. Anufriev ◽  
Akim V. Shmal’ko ◽  
Kyrill Yu. Suponitsky ◽  
Igor B. Sivaev

The simple and efficient method was developed for the one-pot synthesis of B-substituted aryl derivatives of ortho-carborane with functional groups sensitive to organolithium and organomagnesium reagents using 9-iodo-ortho-carborane and generated in situ organozinc compounds. The method proposed was used to prepare a series of 9-aryl-ortho-carboranes, including those containing nitrile and ester groups, 9-RC6H4-1,2-C2B10H11 (R = p-Me, p-NMe2, p-OCH2OMe, o-OMe, p-OMe, o-CN, p-CN, o-COOEt, m-COOEt, and p-COOEt). It was demonstrated that the same approach can be used for synthesis of diaryl derivatives of ortho-carborane 9,12-(RC6H4)2-1,2-C2B10H10 (R = H, p-Me). The solid-state structures of 9-RC6H4-1,2-C2B10H11 (R = p-NMe2, p-OCH2OMe, o-OMe, o-CN, p-CN, m-COOEt, and p-COOEt) and 9,12-(p-MeC6H4)2-1,2-C2B10H10 were determined by single crystal X-ray diffraction.


2017 ◽  
Vol 13 ◽  
pp. 2596-2602 ◽  
Author(s):  
Angélica de Fátima S Barreto ◽  
Veronica Alves dos Santos ◽  
Carlos Kleber Z Andrade

Isocyanide-based multicomponent reactions (IMCRs) allow the construction of relatively complex molecules through a one-pot synthesis. The combination of IMCRs in a consecutive or sequential fashion further extends the complexity of the molecules obtained. Herein, we report the efficient application of this approach to the synthesis of acylhydrazines bearing 1,5-disubstituted tetrazoles. Our strategy was accomplished in only three steps: first, a one-pot hydrazino-Ugi-azide four-component reaction; second a hydrazinolysis and finally an additional hydrazino-Ugi-azide reaction. This sequence provides the title compounds in moderate to excellent yields. The products synthesized herein contain functional groups within their structures that can be easily modified to obtain new acylhydrazino 1,5-disubstituted tetrazoles.


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