66092-09-9Relevant academic research and scientific papers
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
, (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,
Tandem Synthesis of Tetrasubstituted NH Pyrroles from Simple Nitriles
Kim, Hyeongsu,Xuan, Zi,Hyun Kim, Ju
supporting information, p. 3336 - 3340 (2021/09/09)
An efficient tandem route to obtain tetrasubstituted NH pyrroles in a one-pot manner has been developed, staring from simple nitriles, ethyl bromoacetates, and zinc. This reaction involves oxidative dimerization of the zinc bromide complex of β-enaminoesters using cerium ammonium nitrate (CAN) as an oxidant, affording 2,3,4,5-tetrasubstituted pyrroles in yields up to 91%.
Electrochemical Oxidative Cyclization: Synthesis of Polysubstituted Pyrrole from Enamines
Chen, Zhiwei,Shi, Guang,Tang, Wei,Sun, Jie,Wang, Wenxing
supporting information, p. 951 - 955 (2021/02/03)
A conceptually novel method for the preparation of pyrrole is described by electrochemical-oxidation-induced intermolecular annulation via enamines. In a simple undivided cell, based on a sodium acetate-facilitated, polysubstituted pyrrole derivations has been facilely synthesized under external oxidant-free condition. This electrosynthetic approach providing an environmentally benign protocol for C?C bond cross-coupling and oxidative annulation, which features unparalleled broad scope of substrates and practicality.
Visible-light-induced formal [3+2] cycloaddition for pyrrole synthesis under metal-free conditions
Xuan, Jun,Xia, Xu-Dong,Zeng, Ting-Ting,Feng, Zhu-Jia,Chen, Jia-Rong,Lu, Liang-Qiu,Xiao, Wen-Jing
, p. 5653 - 5656 (2014/06/10)
A photocatalytic formal [3+2] cycloaddition of 2H-azirines with alkynes has been achieved under irradiation by visible light in the presence of organic dye photocatalysts. This transformation provides efficient access to highly functionalized pyrroles in good yields and has been applied to the synthesis of drug analogues. A primary trial of photocascade catalysis merging energy transfer and redox neutral reactions was shown to be successful. Photo(chemistry) op: A photocatalytic formal [3+2] cycloaddition of 2H-azirines with alkynes has been established under the irradiation of visible light in the presence of an organic dye. This transformation provides efficient access to highly functionalized pyrroles in good yields and has been applied to the formal synthesis of an inhibitor for HMG-CoA reductase.
Novel photosensitized cyclization reactions of ethyl 3-amino-3-phenyl-2- propenoate derivatives to highly substituted pyrroles
Ishida, Yohsuke,Yoshida, Yuhki,Igarashi, Tetsutaro,Sakurai, Tadamitsu
, p. 1691 - 1698 (2013/09/12)
Irradiation of nitrogen-saturated acetonitrile solutions containing ethyl 3-amino-3-phenyl-2-propenoate derivatives with the (Z)-configuration [(Z)- 1] and 10-methylacridinium perchlorate (MAP) at wavelengths longer than 340 nm afforded the corresponding pyrrole derivatives in good to high yields without exhibiting a profound effect related to the substituents. An analysis of the Stern-Volmer plots for the fluorescence quenching of MAP by (Z)-1 showed that this sensitizer fluorescence is efficiently quenched, and hence electron transfer is confirmed to be involved in the primary process of the MAPsensitized cyclization reactions of 1.
Task-specific basic ionic liquid: A reusable and green catalyst for one-pot synthesis of highly functionalized pyrroles in aqueous media
Yavari, Issa,Kowsari, Elaheh
, p. 897 - 899 (2008/12/22)
A basic functionalized ionic liquid, 1-butyl-3-methylimidazolium hydroxide ([bmim]OH), catalyzed the three-component condensation reaction of acid chlorides, amino acids, and dialkyl acetylenedicarboxylates in water to afford functionalized pyrroles in high yields. Georg Thieme Verlag Stuttgart.
Synthesis of highly substituted pyrroles via oxidative free radical reactions of β-aminocinnamates
Tsai, An-I.,Chuang, Che-Ping
, p. 2235 - 2239 (2007/10/03)
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
Synthesis of 2H-1,4-Thiazine-2,6-dicarboxylates and Their Conversion to 3,4-Pyrroledicarboxylates via Sulfur Extrusion
Lee, Len F.,Howe, Robert K.
, p. 4780 - 4783 (2007/10/02)
The reactions of 3-aminocinnamates 1c,d with S2Cl2 provided 2,5-diaryl-3,4-pyrroledicarboxylates 7c,d in 36-52percent yields whereas the reactions of 3-(perfluoroalkyl)-3-aminoacrylates 1e-h with S2Cl2 or SCl2 gave 3,5-bis(perfluoroalkyl)-2H-1,4-thiazine-
