One-pot amination of cage hydrocarbons

Леонова, М. В.; Skomorokhov, M. Yu.; Моисеев, И. К.; Klimochkin, Yu. N.

doi:10.1134/s1070428015120064

Cited by 29 publications

(4 citation statements)

References 31 publications

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“…The work outlined in this dissertation examines unique routes to prepare 2, 4, 9trithiaadamantane derivatives, some of these routes are related to the previous work just discussed. N-(1-adamantyl) acetamide [22][23][24][25][26][27][28][29][30][31][32][33][34][35][36][37][38][39][40][41]. To a mixture of 99.5% acetonitrile (400 mL, 7.66 mol) and 98% adamantane 2 (277g, 2.0 mol) was added dropwise 98% sulfuric acid (1.56 L, 28.4 mol) with stirring at 25-30°C for 2 h. The reaction mixture was stirred at 60-65°C for an additional 2.5 h. At the end of the reaction, ice water (5.00 L) was added to the reaction mixture and stirred for 1.0 h at 0-5°C.…”

Section: Scheme 3: Alternative Synthesis Of Amantadine (3)mentioning

confidence: 99%

Recent Advances in Process Development of Antiviral Agents Targeting the Influenza Virus: Amantadine-RemantadineDerived Pharmaceutical Agents

Ks¹

2018

OAJPR

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This short review summarizes our work on the process development for the synthesis of amontidine remantadine. The M2 proton channel of the influenza A virus is the target of the anti-influenza drugs amantadine and rimantadine. The effectiveness of these drugs has been dramatically limited by the rapid spread of drug resistant mutations, mainly at sites S31N, V27A and L26F in the pore of the channel. Despite progress in designing inhibitors of V27A and L26F M2, there are currently no drugs targeting these mutated channels in clinical trials. The article traces the evolution of various synthesis approaches and provides a comparison for overall yield efficiency. Amantadine hydrochloride is an antiviral drug used in prevention and treatment of influenza a infections. It has also been used for alleviating early symptoms of Parkinson's disease. Several methods for the preparations of Amantadine hydrochloride have been reported. Overall yields ranging from 50 to 52%. In this article, we describe procedure for the synthesis of Amantadine hydrochloride from via N-(1adamantyl) acetamide with an improved yield of 60% the procedure was also optimized to reduce the use of toxic solvents and reagents, rendering it more environment-friendly. The procedure can be considered as suitable for largescale production of amantadine hydrochloride. Mini ReviewVolume 2 Issue 2

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Section: Scheme 3: Alternative Synthesis Of Amantadine (3)mentioning

confidence: 99%

Recent Advances in Process Development of Antiviral Agents Targeting the Influenza Virus: Amantadine-RemantadineDerived Pharmaceutical Agents

Ks¹

2018

OAJPR

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“…There are many publications reporting the synthesis of amantadine ( 5 ) or amantadine hydrochloride ( 1 ), using different raw materials such as adamantine, − 1-adamantanol, − 1-bromoadamantane, − 1-adamantyl-magesium-bromide, − 1-adamantane-carboxylic-acid, − and tetrahydro-dicyclopentadiene…”

Section: Introductionmentioning

confidence: 99%

Simple and Economical Process for Producing Amantadine Hydrochloride

Thi

Anh

et al. 2022

ACS Omega

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A simple and economical process for producing amantadine hydrochloride (1) on a 250 g scale, an antiviral and anti-Parkinson drug, has been developed. Several methods for the preparation of 1 through intermediate N-(1-adamantyl)-acetamide (4) in four or three steps were reported. These procedures started with adamantine (2) or 1-bromoadamantane (3), acetonitrile, and sulfuric acid by using the Ritter-type reaction to obtain N-(1adamantyl)-acetamide, which was deacetylated to afford 1-aminoadamantane (5) and then the salt formed with anhydrous HCl gives 1 with the overall yield of 1 being 50−58%. In this article, a two-step procedure for the synthesis of 1 from 1-bromadamantane (3) and formamide via N-(1-adamantyl)-formamide (6) in two steps with an overall yield of 88% was reported. In this procedure, the preparation of 6 from 3 is a key step with a yield of 94%, followed by the hydrolysis of 6 with an aq. solution of HCl to give 1 in high yield (93%). The procedure was also carried out under optimal conditions established to reduce the use of toxic reagents or solvents and was carried out in one pot to make it more environmentally friendly. The procedure can be considered as more suitable for the large-scale production of 1. The structures of product 1 and intermediate 6 were confirmed by IR, MS,

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“…Two additional references should have been included in the manuscript as references ( 11 ) and ( 12 ) and are given below.…”

mentioning

confidence: 99%

Correction to “Simple Two-step Procedure for the Synthesis of Memantine Hydrochloride from 1,3-Dimethyl-adamantane”

Vu¹,

Ba²,

Pham³

et al. 2020

ACS Omega

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One-pot amination of cage hydrocarbons

Cited by 29 publications

References 31 publications

Recent Advances in Process Development of Antiviral Agents Targeting the Influenza Virus: Amantadine-RemantadineDerived Pharmaceutical Agents

Recent Advances in Process Development of Antiviral Agents Targeting the Influenza Virus: Amantadine-RemantadineDerived Pharmaceutical Agents

Simple and Economical Process for Producing Amantadine Hydrochloride

Correction to “Simple Two-step Procedure for the Synthesis of Memantine Hydrochloride from 1,3-Dimethyl-adamantane”

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