Reversal of the order of catalytic efficiency of primary and secondary amines in the ionization of a sterically hindered carbon acid

1990 ◽  
Vol 55 (8) ◽  
pp. 2546-2548 ◽  
Author(s):  
Patrick G. Farrell ◽  
Francois Terrier ◽  
Hai Qi Xie ◽  
Taoufik Boubaker
Keyword(s):  
Catalytic Efficiency ◽  
Secondary Amines ◽  
Primary And Secondary Amines ◽  
Sterically Hindered ◽  
Carbon Acid

scholarly journals Cycloruthenated compounds as efficient catalyst for asymmetric hydride transfer reaction

2006 ◽  
Vol 78 (2) ◽  
pp. 457-462 ◽  
Author(s):  
Jean-Baptiste Sortais ◽  
Laurent Barloy ◽  
Claude Sirlin ◽  
André H. M. de Vries ◽  
Johannes G. de Vries ◽  
...  
Keyword(s):  
Transfer Reaction ◽  
Hydride Transfer ◽  
Catalytic Efficiency ◽  
Secondary Amines ◽  
Efficient Catalyst ◽  
Primary And Secondary Amines ◽  
Hydride Transfer Reaction

Cycloruthenated complexes obtained by direct C-H activation of enantiopure aromatic primary and secondary amines are efficient catalysts in asymmetric hydride transfer reaction. Reduction of acetophenone has been achieved rapidly with enantiomeric excesses (ee's) ranging from 38 to 89 %. The importance of Ru-C bond in the catalytic efficiency is highlighted.

Selectivity of nucleophilic addition to and substitution at isothiocyanatocarbonyl group. Reactions of 4-pentinoyl- and 2-(2-propinyl)-4-pentinoyl isothiocyanate with amines and methanol

1987 ◽  
Vol 52 (4) ◽  
pp. 995-1005 ◽  
Author(s):  
Peter Kutschy ◽  
Pavol Kristian ◽  
Milan Dzurilla ◽  
Dušan Koščík ◽  
Róbert Nádaskay
Keyword(s):  
Nucleophilic Substitution ◽  
Carbonyl Group ◽  
Nucleophilic Addition ◽  
Secondary Amines ◽  
Primary Amines ◽  
Primary And Secondary Amines ◽  
Sterically Hindered

4-Pentinoyl isothiocyanate reacts with primary and secondary amines by either nucleophilic addition to N=C=S group to yield the corresponding thioureas, or a nucleophilic substitution at the carbonyl group to give 4-pentinoic acid amides. The less nucleophilic diphenylamine reacts selectively to afford the product of nucleophilic addition only. 2-(2-Propinyl)-4-pentinoyl isothiocyanate, having a sterically hindered carbonyl group, furnished with primary amines a mixture of amides and thioureas, whereas the bulkier secondary amines react selectively to form thioureas only. Both isothiocyanates afford with methanol as a nucleophile exclusively the corresponding O-methyl monothiocarbamates.

The synthesis of sterically hindered amines by a direct reductive amination of ketones

2016 ◽  
Vol 52 (7) ◽  
pp. 1397-1400 ◽  
Author(s):  
Niyaz Z. Yagafarov ◽  
Pavel N. Kolesnikov ◽  
Dmitry L. Usanov ◽  
Valentin V. Novikov ◽  
Yulia V. Nelyubina ◽  
...  
Keyword(s):  
Carbon Monoxide ◽  
Reductive Amination ◽  
Secondary Amines ◽  
Tertiary Amines ◽  
Primary And Secondary Amines ◽  
Sterically Hindered ◽  
Hindered Amines

An atom-economical methodology for the synthesis of sterically hindered tertiary amines was developed, which is based on a complementary Rh- and Ru-catalyzed direct reductive amination of ketones with primary and secondary amines using carbon monoxide as a deoxygenating agent.

Reaction of arylmethylenemalonaldehydes with some nucleophiles

1987 ◽  
Vol 52 (11) ◽  
pp. 2699-2709 ◽  
Author(s):  
Dalimil Dvořák ◽  
Zdeněk Arnold
Keyword(s):  
Inorganic Anions ◽  
Secondary Amines ◽  
Tertiary Amines ◽  
Primary And Secondary Amines ◽  
Dipolar Structure

Reaction of arylmethylenemalonaldehydes with tributylphosphine and tertiary amines affords compounds of dipolar structure whereas reaction with primary and secondary amines leads to 1,4-addition products. Salts of nucleophilic inorganic anions add to arylmethylenemalonaldehydes under formation of salts of substituted malonaldehydes.

Some 1-substitution derivatives of 4-aryl-2,3-dihalogeno-1-naphthols

1984 ◽  
Vol 49 (1) ◽  
pp. 110-121 ◽  
Author(s):  
Jiří Křepelka ◽  
Drahuše Vlčková ◽  
Milan Mělka
Keyword(s):  
Thionyl Chloride ◽  
Oxirane Ring ◽  
Secondary Amines ◽  
Two Phase ◽  
Lytic Effect ◽  
Primary And Secondary Amines ◽  
Phase Medium ◽  
Chloro Derivatives ◽  
Derivatives Of

Alkylation of derivatives of 4-aryl-1-naphthols (I-V) by 2,3-epoxypropyl chloride in methanolic sodium hydroxide gave epoxy derivatives VI, VIII, IX, XI and XII, apart from products of cleavage of the oxirane ring, VII and X. Analogous alkylation of compounds I, IV and V by 2-(N,N-diethylamino)ethyl chloride hydrochloride in a two-phase medium afforded basic ethers XIII to XV. The cleavage of the oxirane ring in compound VI by the action of primary and secondary amines, piperidine and substituted piperazines led to compounds XVI-XXIV. Reaction of thionyl chloride with compounds XXI, XXII and XXIV gave chloro derivatives XXV-XXVII.Exposure of compound XXII to 4-methylbenzenesulfonyl chloride produced compound XXVIII, retaining the secondary alcoholic group. In an antineoplastic screening in vivo none of the compounds prepared had an appreciable activity. Compound XVII, being an analogue of propranolol, was used in the test of isoproterenolic tachycardia, and showed a beta-lytic effect comparable with that of propranol.

ChemInform Abstract: Continuous-Flow Oxidative Cyanation of Primary and Secondary Amines Using Singlet Oxygen.

ChemInform ◽  
2014 ◽  
Vol 45 (30) ◽  
pp. no-no
Author(s):  
Dmitry B. Ushakov ◽  
Kerry Gilmore ◽  
Daniel Kopetzki ◽  
D. Tyler McQuade ◽  
Peter H. Seeberger
Keyword(s):  
Singlet Oxygen ◽  
Continuous Flow ◽  
Secondary Amines ◽  
Primary And Secondary Amines

Catalytic alkyl group exchange reaction of primary and secondary amines

1983 ◽  
Vol 105 (15) ◽  
pp. 5002-5011 ◽  
Author(s):  
Shunichi Murahashi ◽  
Noriaki Yoshimura ◽  
Tatsuo Tsumiyama ◽  
Takeyuki Kojima
Keyword(s):  
Exchange Reaction ◽  
Alkyl Group ◽  
Secondary Amines ◽  
Primary And Secondary Amines

Direct amidation of carboxylic acids with amines under microwave irradiation using silica gel as a solid support

2015 ◽  
Vol 17 (5) ◽  
pp. 3157-3163 ◽  
Author(s):  
Andrea Ojeda-Porras ◽  
Alejandra Hernández-Santana ◽  
Diego Gamba-Sánchez
Keyword(s):  
Fatty Acids ◽  
Microwave Irradiation ◽  
Carboxylic Acids ◽  
Silica Gel ◽  
Solid Support ◽  
Secondary Amines ◽  
Primary And Secondary Amines ◽  
Direct Amidation

A highly improved methodology for the direct amidation of carboxylic acids with amines using silica gel as a solid support and catalyst is described. Several examples using aliphatic, aromatic, unsaturated and fatty acids combined with primary and secondary amines are shown.

ChemInform Abstract: Palladium-Catalyzed Coupling of Functionalized Primary and Secondary Amines with Aryl and Heteroaryl Halides: Two Ligands Suffice in Most Cases.

ChemInform ◽  
2011 ◽  
Vol 42 (15) ◽  
pp. no-no
Author(s):  
Debabrata Maiti ◽  
Brett P. Fors ◽  
Jaclyn L. Henderson ◽  
Yoshinori Nakamura ◽  
Stephen L. Buchwald
Keyword(s):  
Secondary Amines ◽  
Primary And Secondary Amines ◽  
Palladium Catalyzed
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