24512-99-0Relevant articles and documents
Design, synthesis and aromatase inhibitory activities of novel indole-imidazole derivatives
Wang, Rui,Shi, Hong-Fan,Zhao, Jing-Feng,He, Yan-Ping,Zhang, Hong-Bin,Liu, Jian-Ping
, p. 1760 - 1762 (2013)
A series of novel indole-imidazole derivatives have been prepared and evaluated in vitro on the aromatase inhibitory activities. The results suggested that proton or a small electron-withdrawing group at para-position of the phenyl ring would enhance the inhibitory activities and any bulky group should be avoided in order to keep a relative small volume for this kind of molecules.
Visible-Light-Mediated Synthesis of Pyrazines from Vinyl Azides Utilizing a Photocascade Process
Hossain, Asik,Pagire, Santosh K.,Reiser, Oliver
supporting information, p. 1707 - 1714 (2017/11/27)
A convenient method for the synthesis of substituted pyrazines from vinyl azides has been developed. This method is enabled by a dual-energy and electron-transfer strategy by visible-light photocatalysis. Initially, vinyl azides are activated by a triplet sensitization process from an excited ruthenium photocatalyst in the presence of water to form dihydropyrazines, followed by a single-electron-transfer (SET) process under oxygen (air) atmosphere that leads to the tetrasubstituted pyrazines in good to excellent yields.
Indoles via Knoevenagel-Hemetsberger reaction sequence
Heaner Iv, William L.,Gelbaum, Carol S.,Gelbaum, Leslie,Pollet, Pamela,Richman, Kent W.,Dubay, William,Butler, Jeffrey D.,Wells, Gregory,Liotta, Charles L.
, p. 13232 - 13242 (2013/09/02)
A series of substituted indoles have been synthesized by the sequential reaction of aromatic aldehydes with ethyl azidoacetate in the presence of sodium ethoxide to form the corresponding ethyl α-azido-β-arylacrylates (Knoevenagel process) followed by a solvent mediated thermolysis (Hemetsberger process). The isolated yields of the ethyl α-azido-β-arylacrylates were significantly increased when employing the sacrificial electrophile ethyl trifluoroacetate. 1H NMR and coupled 1H-13C NMR analysis of the ethyl α-azido-β-arylacrylates indicate that the condensation is stereospecific - only the Z-isomer could be detected. Solvent mediated thermal treatment of the meta-substituted ethyl α-azido-β- arylacrylates resulted in the formation of both the 5- and 7- substituted indoles - the 5-regioisomer being slightly favored over the 7-regioisomer. Analogous thermal treatment of (2Z, 2Z′)-diethyl 3,3′-(1,3- phenylene)bis(2-azidoacrylate) and (2Z, 2Z′)-diethyl 3,3′-(1,4- phenylene)bis(2-azidoacrylate) exclusively produced pyrroloindoles, diethyl 1,5-dihydropyrrolo[2,3-f]indole-2,6-dicarboxylate and diethyl 1,5-dihydropyrrolo[2,3-f]indole-2,6-dicarboxylate, respectively. Results are also reported which indicate that the α-azido-β-arylacrylates can be used in the subsequent Hemetsberger indolization process without prior purification.
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.
Preparation and Thermal Ring-closure of β-Aryl Vinyl Carbodi-imides: Synthesis of Isoquinoline Derivatives
a. Jose
, p. 1727 - 1731 (2007/10/02)
Reaction of the iminophosphoranes (7)-(9), derived from α-azidocinnamates and triphenylphosphine, with aromatic isocyanates gives either 1-arylaminoisoquinoline-3-carboxylates (10)-(12) or the corresponding carbodi-imides (14)-(18) which by thermal treatm
