135554-03-9Relevant academic research and scientific papers
Formal [4 + 2] benzannulation of 2-alkenyl indoles with aldehydes: A route to structurally diverse carbazoles and bis-carbazoles
Banerjee, Ankush,Guin, Avishek,Saha, Shuvendu,Mondal, Anushree,Maji, Modhu Sudan
, p. 1822 - 1826 (2019)
Construction of structurally diverse carbazoles and bis-carbazoles by protecting-group-free formal [4 + 2]-benzannulation of 2-alkenyl indoles and aldehydes is demonstrated. The sequence of four different reactions is executed in one-pot using readily available and cheap bottle reagents as catalysts rendering this method attractive. The incorporation of inexpensive and environmentally benign molecular oxygen as the oxidant into the final aromatization step enables tolerance of several functional groups.
Rhodium-Catalyzed Direct C—H Alkenylation of Indoles with Alkenyl Borates
Wang, Ze-Tian,Zheng, Zi-Ang,Li, Peng-Jie,Zhou, Chun-Ni,Cai, Shao-Jun,Xiao, Biao,Wang, Liang
, p. 2823 - 2828 (2021)
A new Rh(III)-catalyzed direct C—H alkenylation of 2,3-unsubstitued indoles with alkenyl borates through C—H activation followed by transmetallation was described. This protocol provides an efficient method for the synthesis of terminal C2-alkenylindoles under mild conditions, and also shows broad substrate scope and high functional group tolerance with respect to both components. Furthermore, the C2-alkenylated indole can be easily transformed into carboline derivative, which is an important polycyclic indole moiety in natural products and drug molecules.
Synthetic method of gamma-carboline derivative
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, (2021/06/22)
The embodiment of the invention provides a synthesis method of a gamma-carboline derivative, which comprises the following steps of carrying out C-H alkenylation reaction on a compound I and R2-alkenyl boric acid ester to obtain a compound II, removing a pyrimidine group from the compound II to obtain a compound III, carrying out formylation reaction on the compound III to obtain a compound IV, and carrying out tandem imidization and cyclization reaction on the compound IV to obtain a gamma-carboline derivative shown as a compound V. The reaction formula is shown in the specification, R1 is selected from C1-C6 alkyl, methoxyl, alkoxy, benzyloxy, ester group, acetyl, cyano and halogen, and R2 is selected from C1-C6 alkyl, aryl substituted alkyl, naphthalene ring, heteroaromatic ring, phenyl and substituted phenyl. Indole is used as an initial raw material for de novo construction, and the raw material source is wide; the steps are simple; the reaction efficiency is high; the nitrogen atom of gamma-carboline does not have a substituent group, so that the later-stage structure modification of the nitrogen atom is facilitated.
Rh(i)-catalyzed decarbonylative direct C2-olefination of indoles with vinyl carboxylic acids
Zhang, Lingjuan,Qiu, Ruiying,Xue, Xiao,Pan, Yixiao,Xu, Conghui,Wang, Doudou,Wang, Xinyu,Xu, Lijin,Li, Huanrong
supporting information, p. 12385 - 12388 (2015/01/08)
A general and efficient Rh(i)-catalyzed decarbonylative direct C2-olefination of indoles with vinyl carboxylic acids has been developed. The reaction exhibits excellent functional group tolerance, regioselectivity and stereoselectivity, giving a broad range of C2-alkenylated indoles in good to excellent yields. This journal is
Allenyl azide cycloaddition chemistry. 2,3-Cyclopentennelated indole synthesis through indolidene intermediates
Feldman, Ken S.,Hester II, D. Keith,Iyer, Malliga R.,Munson, Paul J.,Lopez, Carlos Silva,Faza, Olalla Nieto
experimental part, p. 4958 - 4974 (2009/11/30)
(Chemical Equation Presented) The thermal, photochemical, and photochemical/CuI-mediated cascade cyclizations of a range of substituted 1-(2-azidophenyl)-3-alkenylallenes are described. These reactions provide both 1,2- and 2,3-cyclopentennelated indole products in varying ratios. In most cases, high regioselectivity for the 2,3-annelated isomer can be achieved under the h?/CuI conditions. Computational studies of this multistep reaction support the intermediacy of indolidene intermediates whose electrocyclizations (with or without copper present) define the regioselectivity branch point in the sequence.
3-(o-Trifluoroacetamidoaryl)-1-propargylic esters: common intermediates for the palladium-catalyzed synthesis of 2-aminomethyl-, 2-vinylic, and 2-alkylindoles
Ambrogio, Ilaria,Cacchi, Sandro,Fabrizi, Giancarlo,Prastaro, Alessandro
scheme or table, p. 8916 - 8929 (2009/12/07)
3-(o-Trifluoroacetamidoaryl)-1-propargylic esters have been used as common synthetic intermediates for the preparation of a variety of 3-unsubstituted 2-substituted indoles. Treating ethyl 3-(o-trifluoroacetamidoaryl)-1-propargylic carbonates unsubstituted or containing an aryl substituent at the propargylic carbon with piperazines and Pd(PPh3)4 in THF at 80 °C affords 2-(piperazin-1-ylmethyl)indoles in excellent yields. Good to excellent yields of 2-aminomethylindoles are also obtained with other secondary amines. Ethyl 3-(o-trifluoroacetamidoaryl)-1-propargylic carbonates bearing an alkyl substituent at the propargylic carbon and ethyl 3-(o-trifluoroacetamidoaryl)-1-propargylic acetates disubstituted at the propargylic carbon give 2-vinylic indoles with the Pd(OAc)2/PPh3 combination and Et3N in THF at 80 °C. Formation of 2-vinylic indoles is quite stereoselective, generating trans vinylic derivatives, at least with the substrates that we have investigated. In the presence of formic acid, Et3N, and Pd(PPh3)4 in MeCN at 80 °C, ethyl 3-(o-trifluoroacetamidoaryl)-1-propargylic carbonates afford 2-alkylindoles in good to excellent yields.
Allenyl azide cycloaddition chemistry. Synthesis of annelated indoles from 2-(allenyl)phenyl azide substrates
Feldman, Ken S.,Iyer, Malliga R.,Hester II, D. Keith
, p. 3113 - 3116 (2007/10/03)
Thermolysis of 2-(allenyl)phenyl azides leads to a cascade cyclization sequence furnishing both C(2)-C(3) and N-C(2) cyclopentannelated indoles.
