Assembly of 7-carboxylate indoles via the Cu-catalyzed coupling of substituted 2-iodobenzoic acids and substituted hydrazines

Tetrahedron ◽  
2020 ◽  
Vol 76 (1) ◽  
pp. 130794 ◽  
Author(s):  
Quanpeng Wei ◽  
Yunhan Wang ◽  
Jinlong Zhao ◽  
Xiaojing Zhang ◽  
Dawei Ma
1983 ◽  
Vol 61 (8) ◽  
pp. 1806-1812 ◽  
Author(s):  
Alain Turck ◽  
Roland Boutte ◽  
Guy Quéguiner

We have studied the regioselectivity of Michael type additions on tropones attached to quinoxalines, i.e. dialkoxycarbonyl quinoxalinotropones. We used carbon nucleophiles (ethyl malonate and malononitrile), oxygen nucleophiles (sodium methoxide), sulphur nucleophiles (methyl and benzyl mercaptans), and nitrogen nucleophiles (methyl and phenylhydrazine, aniline). We have shown that, in general, these reactions lead to 1,4-monoadditions or to bridged products arising from a bis-1,4-addition process. We have determined the structures of the complexes obtained by comparison to the work of Fohlisch etal. in the homoaromatic series. For the case of substituted hydrazines, we present some evidence on the rearrangement mechanisms proposed by these authors. [Journal translation]


2018 ◽  
Vol 256 ◽  
pp. 489-496 ◽  
Author(s):  
Chunxia Nan ◽  
Jingran Dong ◽  
Hongwu Tian ◽  
Hongmei Shi ◽  
Shigang Shen ◽  
...  

Author(s):  
Hany M. M. DALLONI

A series of 1,2, 4, 5-tetraaza-3-pentenes 4a-j were synthesized by the reaction of appropriate nitrilimines 2 with substituted hydrazines (H2NNHCOR, R=Ph, OMe) 3. Heating the compounds 4a-j with activated charcoal in refluxing benzene oxidized to formazans 5a-j and some formazans 5fj (R = OMe) gave s-tetrazinones 6fj in presence of lithium hydride. The microanalysis and spectral data of the synthesized compounds are in fall agreement with their molecular structure.


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