39167-76-5Relevant academic research and scientific papers
Palladium-Catalyzed Decarboxylative ortho -Amidation of Indole-3-carboxylic Acids with Isothiocyanates Using Carboxyl as a Deciduous Directing Group
Tulichala, R.N. Prasad,Shankar, Mallepalli,Swamy, K.C. Kumara
, p. 4375 - 4383 (2018/04/26)
Palladium-catalyzed ortho-amidation of indole-3-carboxylic acids with isothiocyanates by using the deciduous directing group nature of carboxyl functionality to afford indole-2-amides is demonstrated. Both C-H functionalization and decarboxylation took place in one pot, and hence, this carboxyl group served as a unique, deciduous (or traceless) directing group. This reaction offers a broad substrate scope as demonstrated for several other heterocyclic carboxylic acids like chromene-3-carboxylic acid, imidazo[1,2-a]pyridine-2-carboxylic acid, benzofuran-2-carboxylic acid, pyrrole-2-carboxylic acid, and thiophene-2-carboxylic acid. In the reaction using 2-naphthoic acid, of the two possible isomers, only one isomer of the amide was exclusively formed. The indole-2-amide product underwent palladium-catalyzed C-H functionalization to afford the diindole-fused 2-pyridones by combining two molecules of the indole moiety, with the elimination of an amide group from one of them, attached at the C3-position for the C-C/C-N bond formation. The structures of key products are confirmed by X-ray crystallography.
Synthesis of β- And γ-carbolinones via Pd-catalyzed direct dehydrogenative annulation (DDA) of indole-carboxamides with alkynes using air as the oxidant
Shi, Zhuangzhi,Cui, Yuxin,Jiao, Ning
supporting information; experimental part, p. 2908 - 2911 (2010/09/18)
A palladium-catalyzed direct dehydrogenative annulation (DDA) of indolecarboxamides with internal alkynes via C-H and N-H bond cleavage using air as the oxidant was developed. With this method, both β- and γ-carbolinones can be easily prepared under the mild conditions.
Synthesis, structure-activity relationships and molecular modeling studies of new indole inhibitors of monoamine oxidases A and B
La Regina, Giuseppe,Silvestri, Romano,Gatti, Valerio,Lavecchia, Antonio,Novellino, Ettore,Befani, Olivia,Turini, Paola,Agostinelli, Enzo
experimental part, p. 9729 - 9740 (2009/04/06)
New monoamine oxidase inhibitors were synthesized as indole analogues of a previously reported pyrrole series. Several compounds were potent MAO-A (12, 17, 19-22, 31, 36, and 37) or MAO-B (14, 20, 24, 38, 44, and 46) inhibitors, and had Ki values in the nanomolar concentration range. In particular, 22 (Ki = 0.00092 μM, and SI = 68,478) was exceptionally potent and selective as MAO-A inhibitor. In molecular modeling studies, compounds 22, 24, 44, and 46 positioned the indole ring into an aromatic cavity of MAO-A, and established π-π stacking interactions with Tyr407, Tyr444, and FAD cofactor. However, only compound 22 was able to form hydrogen bonds with FAD, a finding which was in accordance with its potent anti-MAO-A activity. Conversely, 22/MAOB complex was highly unstable during the MD simulation.
Functionalisation of the Alkoxy Group of Alkyl Aryl Ethers. Demethylation, Alkylthiolation and Reduction of 5-Methoxyindoles
Caubere, Catherine,Caubere, Paul,Renard, Pierre,Bizot-Espiart, Jean-Guy,Ianelli, Sandra,et al.
, p. 13433 - 13448 (2007/10/02)
In the presence of AlX3-RSH three kinds of reactions may take place with 5-methoxy indoles: demethylation, alkylthiolation and reduction.The two latter reactions have never been observed to the present, with such reagents.Considerable improvement in the s
