6407-35-8Relevant academic research and scientific papers
Asymmetric and Geometry-Selective α-Alkenylation of α-Amino Acids
Abas, Hossay,Mas-Roselló, Josep,Amer, Mostafa Mahmoud,Durand, Derek J.,Groleau, Robin R.,Fey, Natalie,Clayden, Jonathan
supporting information, p. 2418 - 2422 (2019/02/09)
Both E- and Z-N′-alkenyl urea derivatives of imidazolidinones may be formed selectively from enantiopure α-amino acids. Generation of their enolate derivatives in the presence of K+ and [18]crown-6 induces intramolecular migration of the alkeny
Geometry-Retentive C-Alkenylation of Lithiated α-Aminonitriles: Quaternary α-Alkenyl Amino Acids and Hydantoins
Mas-Roselló, Josep,Hachisu, Shuji,Clayden, Jonathan
supporting information, p. 10750 - 10754 (2017/08/30)
α-Amino nitriles tethered to alkenes through a urea linkage undergo intramolecular C-alkenylation on treatment with base by attack of the lithionitrile derivatives on the N′-alkenyl group. A geometry-retentive alkene shift affords stereospecifically the E
Intramolecular vinylation of secondary and tertiary organolithiums
Lefranc, Julien,Fournier, Anne M.,Mingat, Gaelle,Herbert, Simon,Marcelli, Tommaso,Clayden, Jonathan
supporting information; experimental part, p. 7286 - 7289 (2012/06/16)
Deprotonation of benzylic ureas, carbamates, and thiocarbamates bearing N′-alkenyl substituents generates carbanions which undergo intramolecular migration of the alkenyl group to the carbanionic center. Solvolysis of the urea products generates α-alkenylated amines. With an enantiomerically pure starting urea, migration proceeds stereospecifically, generating in enantiomerically enriched form products containing allylic quaternary stereogenic centers bearing N. Computational and in situ IR studies suggest that the reaction, formally a nucleophilic substitution at an sp2 carbon atom, proceeds by a concerted addition-elimination pathway.
Is an iodine atom almighty as a leaving group for Bu3SnH-mediated radical cyclization? The effect of a halogen atom on the 5-endo-trig radical cyclization of N-vinyl-α-halo amides
Tamura, Osamu,Matsukida, Hana,Toyao, Atsushi,Takeda, Yoshifumi,Ishibashi, Hiroyuki
, p. 5537 - 5545 (2007/10/03)
The effect of a halogen atom as a leaving group on Bu3SnH-mediated 5-endo-trig radical cyclization of N-(cyclohex-1-enyl) α-halo amides was examined. The cyclization of α-chloro amides occurred with a high degree of efficiency, whereas the corresponding α-iodo congeners gave only limited quantities of cyclization products. A detailed study revealed that these phenomena could be attributed to the initial conformations of α-halo amides. The cyclizing ability of α-iodo amides can be restored with Bu3SnCl or Bu3SnF as an additive. The cyclization of an α-iodo amide in the presence of Bu3SnF could be applied to a short-step synthesis of lycoranes featuring sequential 5-endo-trig and 6-endo-trig radical cyclizations.
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. 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.
Reaction of Oximes with Dimethyl Carbonate: A New Entry to 3-Methyl-4,5-disubstituted-4-oxazolin-2-ones
Marques, C. A.,Selva, M.,Tundo, P.,Montanari, F.
, p. 5765 - 5770 (2007/10/02)
The reaction of ketone oximes with dimethyl carbonate (DMC) carried out in an autoclave at 180-190 deg C and in the presence of K2CO3 yields 3-methyl-4,5-disubstituted-4-oxazolin-2-ones.The reaction can be applied to both aliphatic and aromatic ketone oximes, provided that a methylene group be present near the C=N bond.Nonoptimized yields range from 22 to 48percent.The reaction seems to be a sigmatropic rearrangement where DMC plays a key role in causing the initial N-methylation of the oximes.
A Facile Route to 2-Substituted Indoles
Madsen, J.Oe.,Meldal. M.,Mortensen. S.,Olsson, B.
, p. 77 - 82 (2007/10/02)
Imines, derived from cyclohexanone and alkylamines, react with α-chloroacrylonitrile in the presence of triethylamine to give products which upon pyrolysis afford 1-alkyl-4,5,6,7-tetrahydroindoles.Substitution at the 2-position of these compounds followed
