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.

Palladium(II)-Catalyzed C(sp2)–H Carbonylation of Sterically Hindered Amines with Carbon Monoxide

2018 ◽  
Vol 20 (20) ◽  
pp. 6530-6533 ◽  
Author(s):  
Xiu-Fen Cheng ◽  
Tao Wang ◽  
Yan Li ◽  
Yun Wu ◽  
Jie Sheng ◽  
...  
Keyword(s):  
Carbon Monoxide ◽  
Sterically Hindered ◽  
Hindered Amines

Oxidative coupling of amines and carbon monoxide catalyzed by palladium complexes. Mono- and double carbonylation reactions promoted by iodine compounds

1990 ◽  
Vol 68 (9) ◽  
pp. 1544-1547 ◽  
Author(s):  
Ilan Pri-Bar ◽  
Howard Alper
Keyword(s):  
Carbon Monoxide ◽  
Oxidative Coupling ◽  
Room Temperature ◽  
Palladium Complexes ◽  
Secondary Amines ◽  
Primary Amines ◽  
Palladium Acetate ◽  
Principal Product ◽  
Iodine Compounds ◽  
Primary And Secondary Amines

Iodine is an effective promoter for the carbonylation of primary and secondary amines to ureas using palladium acetate as the catalyst and a base (e.g. K2CO3) in acetonitrile (3 h at 95 °C and 2.7 atm). Oxamides are formed in excellent yields when secondary amines are carbonylated in the presence of iodide ion and oxygen, while primary amines give ureas as the principal product at 95 °C, and oxamide at room temperature. Keywords: oxamides, ureas, double carbonylation, amines.

Cyclization kinetics and mechanism of N-benzoyl-N'-(1,2-dimethyl-3-oxo-1-butenyl)thiourea

1983 ◽  
Vol 48 (2) ◽  
pp. 578-585 ◽  
Author(s):  
Jaromír Kaválek ◽  
Tomáš Potěšil ◽  
Vojeslav Štěrba
Keyword(s):  
Hydrochloric Acid ◽  
Secondary Amines ◽  
Tertiary Amines ◽  
Cyclization Product ◽  
Ph Values ◽  
Hydroxyl Ion ◽  
Primary And Secondary Amines ◽  
Acids And Bases ◽  
Cyclization Kinetics ◽  
Kinetics Of

Cyclization kinetics of N-benzoyl-N'-(1,2-dimethyl-3-oxo-1-butenyl)thiourea have been studied in aqueous and methanolic solutions of acids and bases. In all cases the cyclization product is 4,5,6-trimethyl-2,5-dihydro-2-thioxopyrimidine or its protonated or deprotonated forms. In dilute methanolic and aqueous hydrochloric acid the substrate reacts in its monoprotonated form. The cyclization in basic media is catalyzed by methoxide or hydroxyl ion and also by primary and secondary amines at such pH values where the catalysis by lyate ion is practically insignificant. Tertiary amines and acetate ion do not catalyze the cyclization.

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