33629-95-7Relevant academic research and scientific papers
Transition-Metal-Free Synthesis of 1,2-Disubstituted Indoles
Chesnokov, Gleb A.,Ageshina, Alexandra A.,Topchiy, Maxim A.,Nechaev, Mikhail S.,Asachenko, Andrey F.
, p. 4844 - 4854 (2019)
Herein, we report a new transition-metal-free robust and cost-effective method for synthesis of 1,2-disubstituted indoles from easily available unactivated (i.e. without EWG, PPh3 or SiR3 groups) tertiary amides. Scope of synthetic applicability of the presented protocol was shown on 23 examples of 1,2-disubstituted indoles with different substitution patterns obtained in good to excellent yields. The reported method turned out to be especially effective for synthesis of N-arylated 2-CF3-indoles. Moreover, this approach can be performed in a one-pot two-step manner directly from commercially available secondary amines. Mechanistic studies showed that acyl transfer might be an important step in the course of the reaction. Viability of the presented approach for benzofurans and benzothiophenes synthesis was also discussed.
Experimental evidence for intramolecular ipso substitution of alkyl groups
Zubkov, Fedor I.,Nikitina, Eugenia V.,Kouznetsov, Vladimir V.,Duarte, Luz Dary Avellaneda
, p. 5064 - 5074 (2007/10/03)
An acid-mediated intramolecular Friedel-Crafts intramolecular alkene alkylation of the ortho-alkyl group in the N-aryl-amino moiety of various N-(1-allylcycloalkyl)-N-arylamines resulting in alkyl-substituted 3′,4′-dihydro-1′H-spiro[cycloalkane-1,2′-quino
Method for preparing aromatic secondary amino compound
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, (2008/06/13)
Disclosed are (1) a method for preparing an aromatic secondary amino compound which comprises reacting an N-cyclohexylideneamino compound in the presence of a hydrogen moving catalyst and a hydrogen acceptor by the use of a sulfur-free polar solvent and/or a cocatalyst, and (2) a method for preparing an aromatic secondary amino compound which comprises reacting cyclohexanone or a nucleus-substituted cyclohexanone, an amine and a nitro compound corresponding to the amine in a sulfur-free polar solvent in the presence of a hydrogen moving catalyst, a cocatalyst being added or not added. In a further aspect, a method is provided for the preparation of aminodiphenylamine by reacting phenylenediamine and cyclohexanone in the presence of a hydrogen transfer catalyst in a sulfur-free polar solvent while using nitroaniline as a hydrogen acceptor.
Method for preparing aromatic secondary amino compound
-
, (2008/06/13)
Disclosed are (1) a method for preparing an aromatic secondary amino compound which comprises reacting an N-cyclohexylideneamino compound in the presence of a hydrogen moving catalyst and a hydrogen acceptor by the use of a sulfur-free polar solvent and/or a cocatalyst, and (2) a method for preparing an aromatic secondary amino compound which comprises reacting cyclohexanone or a nucleus-substituted cyclohexanone, an amine and a nitro compound corresponding to the amine in a sulfur-free polar solvent in the presence of a hydrogen moving catalyst, a cocatalyst being added or not added.
SYNTHESIS AND NITRATION OF 4,6(4,8)-DIMETHYL-4-METHYL-6(8)-METHOXY-1,2,3,4-TETRAHYDROSPIRO
Kuznetsov, V. V.,Pal'ma, A.,Aliev, A. E.,Fernandes, M.,Prostakov, N. S.,Varlamov, A. V.
, p. 671 - 675 (2007/10/02)
The cyclization of 1-allyl-1-arylaminocyclohexanes under conditions of acid catalysis afforded 1,2,3,4-tetrahydro-4-methylspiro methyl (methoxy)-substituted in the phenylene ring.Their mono- and dinitro derivatives were synthesiz
