69640-22-8Relevant academic research and scientific papers
Synthesis of highly substituted pyrroles via oxidative free radical reactions of β-aminocinnamates
Tsai, An-I.,Chuang, Che-Ping
, p. 2235 - 2239 (2006)
Oxidative free radical reactions of β-aminocinnamates are described. Imine radicals produced by tetra-n-butylammonium cerium(IV) nitrate (TBACN) oxidation of enamines undergo efficient addition to the C-C double bond of β-aminocinnamates. This TBACN media
Trifluoroethanol as a Unique Additive for the Chemoselective Electrooxidation of Enamines to Access Unsymmetrically Substituted NH-Pyrroles
Baidya, Mrinmay,De Sarkar, Suman,Maiti, Debabrata,Roy, Lisa
supporting information, (2021/12/23)
An electrochemical method for the synthesis of unsymmetrically substituted NH-pyrroles is described. The synthetic strategy comprises a challenging heterocoupling between two structurally diverse enamines via sequential chemoselective oxidation, addition,
Orthogonal synthesis of pyrroles and 1,2,3-triazoles from vinyl azides and 1,3-dicarbonyl compounds
Ng, Eileen Pei Jian,Wang, Yi-Feng,Hui, Benjamin Wei-Qiang,Lapointe, Guillaume,Chiba, Shunsuke
experimental part, p. 7728 - 7737 (2011/10/13)
Tri- and tetrasubstituted N-H pyrroles were prepared by the simple treatment of vinyl azides with 1,3-dicarbonyl compounds in toluene at 100 °C via 2H-azirine intermediates generated in situ. When the reactions of vinyl azides and 1,3-dicarbonyl compounds were performed in DMF in the presence of a catalytic amount of K2CO3, 1-vinyl-1,2,3-triazoles were obtained via 1,3-dipolar cycloaddition. These methodologies exploited orthogonal modes of chemical reactivity of vinyl azides, which could be achieved by slight modification of the reaction conditions.
Synthesis of polysubstituted N-H pyrroles from vinyl azides and 1,3-dicarbonyl compounds
Chiba, Shunsuke,Wang, Yi-Feng,Lapointe, Guillaume,Narasaka, Koichi
, p. 313 - 316 (2008/09/19)
(Chemical Equation Presented) Two synthetic methods for tetra- and trisubstituted N-H pyrroles are presented: (i) the thermal pyrrole formation by the reaction of vinyl azides with 1,3-dicarbonyl compounds via the 1,2-addition of 1,3-dicarbonyl compounds to 2H-azirine intermediates generated in situ from vinyl azides; (ii) the Cu(II)-catalyzed synthesis of pyrroles from α-ethoxycarbonyl vinyl azides and ethyl acetoacetate through the 1,4-addition reaction of the acetoacetate to the vinyl azides. By applying these two methods, regioisomeric pyrroles can be prepared selectively starting from the same vinyl azides.
