Synthesis of Cyanamides via a One-Pot Oxidation–Cyanation of Primary and Secondary Amines

2019 ◽  
Vol 21 (5) ◽  
pp. 1268-1272 ◽  
Author(s):  
Nadine Kuhl ◽  
Saurin Raval ◽  
Ryan D. Cohen
Keyword(s):  
Secondary Amines ◽  
One Pot ◽  
Primary And Secondary Amines

scholarly journals Rhodium(III)-Catalyzed Three-Component 1,2-Diamination of Unactivated Terminal Alkenes

Synthesis ◽  
2019 ◽  
Vol 52 (08) ◽  
pp. 1247-1252 ◽  
Author(s):  
Sumin Lee ◽  
Young Jin Jang ◽  
Erik J. T. Phipps ◽  
Honghui Lei ◽  
Tomislav Rovis
Keyword(s):  
Good Yield ◽  
Ring Opening ◽  
Secondary Amines ◽  
One Pot ◽  
Rapid Access ◽  
Primary And Secondary Amines ◽  
Terminal Alkenes ◽  
Broad Array ◽  
Vicinal Diamines

We report a three-component diamination of simple unactivated alkenes using an electrophilic nitrene source and amine nucleo­philes. The reaction provides rapid access to 1,2-vicinal diamines from terminal alkenes through a one-pot protocol. The transformation proceeds smoothly with excellent tolerance for a broad array of primary and secondary amines, affording the desired products in good yield and regioselectivity. The mechanism is proposed to proceed through a Rh(III)-catalyzed aziridination of alkenes with subsequent ring opening by primary or secondary amines.

Catalyst-Free One-Pot Reductive Alkylation of Primary and Secondary Amines and N,N-Dimethylation of Amino Acids Using Sodium Borohydride in 2,2,2-Trifluoroethanol

Synthesis ◽  
2010 ◽  
Vol 2011 (03) ◽  
pp. 490-496 ◽  
Author(s):  
Mahmood Tajbakhsh ◽  
Rahman Hosseinzadeh ◽  
Heshmatollah Alinezhad ◽  
Somayeh Ghahari ◽  
Akbar Heydari ◽  
...  
Keyword(s):  
Amino Acids ◽  
Sodium Borohydride ◽  
Secondary Amines ◽  
Reductive Alkylation ◽  
One Pot ◽  
Catalyst Free ◽  
Primary And Secondary Amines

Synthesis of α-amino nitriles through one-pot selective Ru-photocatalyzed oxidative cyanation of amines

2020 ◽  
Vol 7 (17) ◽  
pp. 3092-3105 ◽  
Author(s):  
Igor Echevarría ◽  
Mónica Vaquero ◽  
Roberto Quesada ◽  
Gustavo Espino
Keyword(s):  
Secondary Amines ◽  
Excellent Performance ◽  
One Pot ◽  
New Family ◽  
Primary And Secondary Amines

A new family of Ru(ii) photocatalysts exhibits excellent performance in the efficient and eco-friendly one-pot preparation of α-amino nitriles from primary and secondary amines.

ChemInform Abstract: Catalyst-Free One-Pot Reductive Alkylation of Primary and Secondary Amines and N,N-Dimethylation of Amino Acids Using Sodium Borohydride in 2,2,2-Trifluoroethanol.

ChemInform ◽  
2011 ◽  
Vol 42 (23) ◽  
pp. no-no
Author(s):  
Mahmood Tajbakhsh ◽  
Rahman Hosseinzadeh ◽  
Heshmatollah Alinezhad ◽  
Somayeh Ghahari ◽  
Akbar Heydari ◽  
...  
Keyword(s):  
Amino Acids ◽  
Sodium Borohydride ◽  
Secondary Amines ◽  
Reductive Alkylation ◽  
One Pot ◽  
Catalyst Free ◽  
Primary And Secondary Amines

scholarly journals One-pot synthesis of GABA amides via the nucleophilic addition of amines to 3,3-disubstituted cyclopropenes

2015 ◽  
Vol 13 (34) ◽  
pp. 8993-8995 ◽  
Author(s):  
Vladimir A. Maslivetc ◽  
Marina Rubina ◽  
Michael Rubin
Keyword(s):  
Double Bond ◽  
Nucleophilic Addition ◽  
Ring Opening ◽  
Secondary Amines ◽  
One Pot ◽  
One Pot Synthesis ◽  
Primary And Secondary Amines ◽  
Donor Acceptor

A one-pot synthesis of various GABA amides has been demostrated, employing the nucleophilic addition of primary and secondary amines across the double bond of cyclopropene-3-carboxamides, followed by ring-opening of the resulting donor–acceptor cyclopropanes and subsequent in situ reduction of enamine intermediates.

scholarly journals Straightforward One-Pot Syntheses of Silylamides of Magnesium and Calcium via an In Situ Grignard Metalation Method

Synthesis ◽  
2018 ◽  
Vol 51 (05) ◽  
pp. 1115-1122 ◽  
Author(s):  
Sven Krieck ◽  
Philipp Schüler ◽  
Jan Peschel ◽  
Matthias Westerhausen
Keyword(s):  
Large Scale ◽  
Room Temperature ◽  
Secondary Amines ◽  
Complex Calcium ◽  
One Pot ◽  
Primary And Secondary Amines ◽  
Catalytic Applications

Calcium bis[bis(trimethylsilyl)amide] (Ca(HMDS)2) is a widely used reagent in diverse stoichiometric and catalytic applications. These processes necessitate a straightforward and large-scale access of this complex. Calcium does not react with primary and secondary amines, but the addition of excess bromoethane to a mixture of calcium turnings and amines in THF at room temperature yields the corresponding calcium bis(amides), calcium bromide and ethane. This in situ Grignard metalation method (iGMM) allows the preparation of calcium bis(amides) from secondary and primary trialkylsilyl-substituted amines and anilines on a multigram scale.1 Background2 The In Situ Grignard Metalation Method (iGMM)3 Properties of [(thf)2M(HMDS)2]4 Applications and Perspective

Copper-catalyzed one-pot oxidative amidation of alcohol to amide via C–H activation

RSC Advances ◽  
2016 ◽  
Vol 6 (92) ◽  
pp. 89413-89416 ◽  
Author(s):  
Jiajia Gu ◽  
Zheng Fang ◽  
Yuhang Yang ◽  
Zhao Yang ◽  
Li Wan ◽  
...  
Keyword(s):  
Secondary Amines ◽  
One Pot ◽  
Mild Conditions ◽  
Primary And Secondary Amines ◽  
Aromatic Alcohols ◽  
Oxidative Amidation

Copper-catalyzed one-pot oxidative amidation of both aliphatic and aromatic alcohols with N-chloramines, prepared in situ from many types of primary and secondary amines, to form amides under mild conditions.

scholarly journals Selenoxide Elimination Triggers Enamine Hydrolysis to Primary and Secondary Amines: A Combined Experimental and Theoretical Investigation

Molecules ◽  
2021 ◽  
Vol 26 (9) ◽  
pp. 2770
Author(s):  
Giovanni Ribaudo ◽  
Marco Bortoli ◽  
Erika Oselladore ◽  
Alberto Ongaro ◽  
Alessandra Gianoncelli ◽  
...  
Keyword(s):  
Mass Spectrometry ◽  
Density Functional ◽  
Underlying Mechanism ◽  
Model Reaction ◽  
Bioactive Molecules ◽  
Secondary Amines ◽  
One Pot ◽  
Functional Theory ◽  
Primary And Secondary Amines ◽  
Novel Strategy

We discuss a novel selenium-based reaction mechanism consisting in a selenoxide elimination-triggered enamine hydrolysis. This one-pot model reaction was studied for a set of substrates. Under oxidative conditions, we observed and characterized the formation of primary and secondary amines as elimination products of such compounds, paving the way for a novel strategy to selectively release bioactive molecules. The underlying mechanism was investigated using NMR, mass spectrometry and density functional theory (DFT).

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.

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