Microwave assisted N-chlorination of secondary amides

Katritzky, Alan R.; Majumder, Suman; Jain, Ritu

doi:10.3998/ark.5550190.0004.c09

Cited by 10 publications

(5 citation statements)

References 25 publications

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“…There are several methods for the preparation of chloroamide derivatives which use some reagents such as trichloroisocyanuric acid, [ 31 ] N‐chlorobenzotriazole, [ 32 ] and chloroacetyl chloride [ 33 ] (Figure 7). In this research, compound 8 reacted with chloroacetyl chloride in the presence of triethylamine to form either 10 or 11 .…”

Section: Resultsmentioning

confidence: 99%

Retracted: Design and synthesis of two epoxide derivatives from 3‐ethynylaniline

Figueroa‐Valverde

Francisco

María

et al. 2021

Journal of Heterocyclic Chem

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For several years ago, several epoxide derivatives have been prepared using different methods; however, some protocols use reagents which could be expensive and require specials conditions. The aim of this investigation was to prepare two new epoxide‐derivatives from 3‐ethynylaniline using some reactions such as oximation, acetylation, 2 + 2 addition, functionalized chloroamides, and epoxidation via Darzens reaction. The chemical characteristics of epoxide derivatives were determinate through a spectroscopic and spectrometric analysis. In conclusion, it is noteworthy that the reactions used in this study do not involve expensive reagents or special conditions for the synthesis of epoxide derivatives.

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Section: Resultsmentioning

confidence: 99%

Retracted: Design and synthesis of two epoxide derivatives from 3‐ethynylaniline

Figueroa‐Valverde

Francisco

María

et al. 2021

Journal of Heterocyclic Chem

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“…It is noteworthy that some chloroamide analogs were synthesized using trichloroisocyanuric Acid [29], N-chlorobenzotriazole [30], chloroacetyl chloride [31,32] and others. In this investigation, two steroid-chloroamide analogs were synthetized via reaction of 5 or 6 with chloroacetyl chloride in the presence of triethylamine (Figure 3).…”

Section: Synthesis Of Two Chloroamide Derivativesmentioning

confidence: 99%

Experimental and theoretical evaluation of two indol-steroid-cyclobuta-imidazole derivatives as antibacterial drugs

2019

Biointerface Res Appl Chem

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There some for treatment of infectios deseasses; however, some drugs can induce several adverse effects. The aim of this study was synthesizing and to determinate the antibacterial activity of two indol-steroid-cyclobuta-imidazole complex (compound 11 and 12) against Staphylococcus aureus, Escherichia colli and Klebsiella pneumoniae in a minimum inhibitory concentration (MIC) model, using gentamicin, ciprofloxacin, cefotaxime as controls. The following stage involved the theoretical evaluation of the interaction of both compounds 11 and 12 with the β-lactamase enzyme (5f1g) using a docking software. The data found indicate that compound 12 decrease the growth bacterial of Staphylococcus aureus, Escherichia colli and Streptococcus pneumoniae in comparison with the compound 11 and this effect only was similar to cefotaxime Other theoretical data indicated that compound 12 could interact with different type of amino acids residues such as Ser61, Leu116, Gln117, Asp120, Tyr147, Asn149, Ser209, Tyr218, Thr318, Asn342 involved in the surface of 5f1g compared with 11. These data indicate that; i) the steroid derivative (12) show better affinity by the 5f1g protein in comparison with compound 11 which is translated as higher antibacterial activity; ii) this compound is particularly interesting because could constitute a novel therapy as antibacterial agent.

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“…2). It is important to mention that although many procedures for the formation of chloroamides are known in the literature, for example the reaction of amine with trichloroisocyanuric acid 19 or secondary amide with N-chlorobenzotriazoleto form a chloroamide derivative 20 . In addition, since several years ago, have been prepared some chloroamides using chloroacetyl chloride 21,22 .…”

Section: Resultsmentioning

confidence: 99%

Design and Synthesis of Estrogen Derivative

Figueroa‐Valverde¹,

Díaz-Cedillo²,

García-Cervera³

et al. 2014

Asian J. Chem.

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Some estrogen derivatives have been developed for use in different biological and analytical methods 1-3 . For example, there are studies which show the synthesis of 2-alkylsulfanyl estrogens which are achieved by a directed ortho-lithiation reaction of suitably protected estrone followed by disulfide quench and final deprotection 4 . Other data showed the synthesis of nitrile derivatives of estrogens by reaction of 7α-cyano-19-nortestosterone with copper(II ) bromide in acetonitrile at room temperature, resulting in aromatization of the A-ring of steroid 5 . In addition, other estradiol derivative (17α-(ruthenocenylmethyl)estra-1,3,5(10)-trien-3,17β-diol) was synthetized by the reaction between 17β-spiro-oxiranyl estradiol and lithium ruthenocenyl in THF 6 . Also, several 17β-O-alkyl ethers (methyl, ethyl, propyl, butyl, hexyl and octyl) of estradiol were obtained from 3-O-benzyl-17β-estradiol with sodium hydride/ alkyl halide, followed by the removal of O-benzyl protecting group via catalytic transfer hydrogenation 7 . Additionally, there are some reports which shown the synthesis of an estradiol derivative by the Reformatsky reaction of 3,17β-bis [(2trimethylsilyl

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Microwave assisted N-chlorination of secondary amides

Abstract: Acyclic (1a-c), and cyclic (4a-f) secondary amides are N-chlorinated by N-chlorobenzotriazole under 15-20 minutes of microwave heating to give the corresponding N-chloro secondary amides (3a-c, 5a-f) in yields of 50-80%.

Cited by 10 publications

References 25 publications

Retracted: Design and synthesis of two epoxide derivatives from 3‐ethynylaniline

Retracted: Design and synthesis of two epoxide derivatives from 3‐ethynylaniline

Experimental and theoretical evaluation of two indol-steroid-cyclobuta-imidazole derivatives as antibacterial drugs

Design and Synthesis of Estrogen Derivative

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