Relevant bibliographies by topics / Morpholines – chemical synthesis

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  1. Journal articles
  2. Dissertations / Theses

Academic literature on the topic 'Morpholines – chemical synthesis'

Author: Grafiati
Published: 4 June 2021
Last updated: 1 February 2022

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Journal articles on the topic "Morpholines – chemical synthesis"

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Reddy, B. Jayachandra, and M. C. Somasekhara Reddy. "Ultrasonicated Synthesis ofN-Benzyl-2,3-substituted Morpholines, via the Mitsunobu Diol Cyclisation." E-Journal of Chemistry 7, no. 4 (2010): 1184–89. http://dx.doi.org/10.1155/2010/931015.

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A facile five step synthesis ofN-benzyl-2,3-substituted morpholines (i-iii) was performed. The key steps were microwave assisted Friedel-crafts acylation and diol cyclization carried out via an ultra sonication of Mitsunobu reaction using DEAD (diethylazodicarboxylate), TPP in THF for 1 h. The morpholine products were generated as diasteriomers (iiandiii) which has been separated by the column chromatography to good yield. The structure of compounds (i-iii) has been characterized by the spectral and chemical studies.
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Magerramov, A. M., M. N. Magerramov, Kh A. Makhmudova, and G. I. Alizade. "Synthesis of N-Substituted Oxazolidines and Morpholines." Russian Journal of Applied Chemistry 78, no. 8 (August 2005): 1301–5. http://dx.doi.org/10.1007/s11167-005-0502-x.

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Beng, Timothy K., Abdikani Omar Farah, and Victoria Shearer. "Modular synthesis and transition metal-free alkynylation/alkenylation of Castagnoli–Cushman-derived N,O- and N,S-heterocyclic vinyl chlorides." RSC Advances 10, no. 61 (2020): 37153–60. http://dx.doi.org/10.1039/d0ra06619b.

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A functional group-tolerant and transition metal-free coupling of novel N,O- and N,S-heterocyclic vinyl chlorides, which affords fully carbosubstituted dihydro-1,4-oxazines/thiazines as well as bicyclic morpholines, is described.
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Cera, Gianpiero, Michel Chiarucci, and Marco Bandini. "Accessing chemical diversity by stereoselective gold-catalyzed manipulation of allylic and propargylic alcohols." Pure and Applied Chemistry 84, no. 8 (February 3, 2012): 1673–84. http://dx.doi.org/10.1351/pac-con-11-09-05.

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The combined use of asymmetric Au(I) catalysis with allylic as well as propargylic alcohols proved to be a competent synthetic tool, toward the realization of complex molecular organic architectures in a stereochemically defined manner. In particular, allylic alcohols have been utilized as alkylating agents in the synthesis of tetrahydrocarbazoles/carbolines and morpholines by means of new C–C and C–X bond-forming processes. Analogously, the direct activation of indole-propargylic alcohols with cationic Au complexes opened a direct access to tetracyclic fused indolines in a highly stereoselective manner.
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Rasulov, Ch K., A. G. Azizov, F. A. Nabiev, S. T. Rustamov, and A. S. Askerova. "Synthesis of N-[2-hydroxy-4(5)-methyl- and -5-(methylcyclohexyl)benzyl]morpholines as antioxidants for transformer oils." Russian Journal of Applied Chemistry 83, no. 12 (December 2010): 2140–43. http://dx.doi.org/10.1134/s107042721012013x.

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6

Journal, Baghdad Science. "Synthesis, Characterization and Study the Biological Activity of New Morpholine Derivative." Baghdad Science Journal 12, no. 4 (December 6, 2015): 761–73. http://dx.doi.org/10.21123/bsj.12.4.761-773.

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A new series of morpholine derivative were prepared by reacting the morpholine with ethyl chloro acetate in the presence triethylamine as an catalyst and benzene as a solvent gave the ethyl morpholin-4-ylacetate reaction with hydrazine hydrate and ethanol as a solvent gave the 2-(morpholin-4-yl)acetohydrazide gave series of Schiff base were prepared by reacting 2-(morpholin-4- yl)acetohydrazide with different aromatic aldehydes and ketons . The new series of (3-9 )were synthesis by reaction of Schiff base (10-14) with chloroacetyl chloride, triethyl amine as an catalyst and 1,4dioxane as a solvent .The chemical structures of the synthesis compound were identified by spectral methods their [ IR ,1H-NMR and 13C-NMR ].The synthesised compounds were screened for antibacterial activity and antifungal activity promising by disc diffusion method by measuring the zone of inhibition and the results were compared to standard drugs ciprofloxacin .
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7

D’hooghe, Matthias, Stijn Dekeukeleire, Erika Leemans, and Norbert De Kimpe. "Use of functionalized β-lactams as building blocks in heterocyclic chemistry." Pure and Applied Chemistry 82, no. 9 (June 4, 2010): 1749–59. http://dx.doi.org/10.1351/pac-con-09-09-39.

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β-Lactams represent flexible building blocks suitable for the preparation of a large variety of nitrogen-containing target compounds. In the present study, the formerly neglected synthetic potential of 4-haloalkyl-β-lactams has been elaborated in detail with a focus on the preparation of different mono- and bicyclic heterocycles. A first approach involved ring transformations of these halogenated building blocks toward stereodefined aziridines, azetidines, pyrrolidines, and piperidines via intermediate aziridinium or azetidinium ions. In a second part, novel and stereoselective entries into 1,4- and 3,4-fused bicyclic β-lactams were developed through either a radical or an ionic cyclization protocol. Furthermore, the ring enlargement of halogenated β-lactams into functionalized mono- and bicyclic pyrrolidin-2-ones was established as the aza-analog of the cyclobutylmethylcarbenium ion to cyclopentylcarbenium ion rearrangement. Finally, chiral versions toward azetidin-2-ones and ring transformation products were elaborated, involving the synthesis of 3(S)-alkoxy-4(S)-[1(S)-chloroethyl]azetidin-2-ones and the preparation of bicyclic β-lactams annelated to piperazines, morpholines, and diazepanes.
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8

Hermecz, István, Andrea Sánta-Csutor, Csaba Gönczi, Gergely Héja, Éva Csikós, Kálmán Simon, Ágota Smelkó-Esek, and Benjámin Podányi. "Chemical development of the vasopressin receptor 2 antagonist SR-121463." Pure and Applied Chemistry 73, no. 9 (September 1, 2001): 1401–9. http://dx.doi.org/10.1351/pac200173091401.

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A facile convergent total synthesis of the selective, potent, and orally active V2 non-peptide antagonist, SR-121463, was developed by modification of the discovery route. One of the late intermediates, the sulfonyl chloride 1, was synthesized from 3-hydroxybenzoic acid (19) by regioselective sulfonation, O-methylation and amidation in four steps. Another late intermediate, indolin-2-one 2, was prepared from p-phenetidine (8) through the indolin-2-one 16, where the cyclohexanone moiety of 27 was introduced into the active 3-methylene group of 16 by sequential transformation using methyl acrylate and KOtBu. After formation of the cyclic ketal moiety of 13, its ring-opening was achieved by using NaBH4 in the presence of CCl3COOH. The morpholino group in 2 was introduced in accordance with the discovery approach, starting from the 2-hydroxyethoxy derivative 14 through the tosyloxy derivative 15 with morpholine in a one-pot reaction. In this way, the indolin-2-one 2 was synthesized from 8 in six steps. Finally, acylation of the indolin-2-one 2 was achieved with the sulfonyl chloride 1 in the presence of KOtBu in dimethyl sulfoxide (DMSO) at room temperature. This synthetic route proved to be applicable for the large-scale synthesis of SR-121463.
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Kumar, Praveen, Jai Prakash Kumar, Juhi Barnwal, and Ritu Singh. "Design, Synthesis and Molecular Docking Studies of 4-{3-[2-(2-Morpholin-4-yl-ethoxy)phenyl]-5-phenyl-pyrazol-1-yl}-benzenesulfonamide as Anti-Breast Cancer Agent." Asian Journal of Organic & Medicinal Chemistry 5, no. 4 (December 31, 2020): 301–6. http://dx.doi.org/10.14233/ajomc.2020.ajomc-p271.

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Novel 4-{3-[2-(2-morpholin-4-yl-ethoxy)phenyl]-5-phenyl-pyrazol- 1-yl}benzenesulfonamide (7) was synthesized and evaluated for its anti-breast cancer activity. It was prepared by cyclocondensation reaction of morpholine-substituted β-diketone, 1-[2-(2-morpholin-4-yl-ethoxy)- phenyl]-3-phenyl-propane-1,3-dione (3) with 4-hydrazinobenzenesulfonamide hydrochloride (6). Chemical structure of titled compound (7) was confirmed by FTIR, 1H & 13C NMR and HRMS spectroscoic analyses. The anticancer activity of titled compound 7 was evaluated against MCF-7 breast cancer cell line by MTT assay. Molecular docking was performed to predict its plausible binding with the estrogen receptor α(ERα) using Molecular Operating Environment 2019.0101 software. The MTT assay results showed that titled compound 7 exhibited better anticancer activity against MCF7 cells (IC50: 4.25 μM) than standard drug, 4-hydroxytamoxifen (IC50: 8.22 μM). Results of molecular docking studies were found in good agreement with the results of anticancer evaluation, as the binding score of titled compound 7 (-16.9872 kcal/mol) was lower as compared to 4-hydroxytamoxifen (-15.1112 kcal/mol). The new cationic interaction of titled compound 7 with Trp383 and hydrogen bonding interaction with Phe404 in active site of ERα made its anticancer activity better than 4-hydroxytamoxifen. Thus, 4-{3-[2-(2-morpholin-4-yl-ethoxy)phenyl]-5-phenyl-pyrazol- 1-yl}benzenesulfonamide (7) was emerged as a potent anti-breast cancer agent.
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10

Barker, David, Benjamin Dickson, Nora Dittrich, and Claire E. Rye. "An acyl-Claisen approach to the synthesis of lignans and substituted pyrroles." Pure and Applied Chemistry 84, no. 7 (March 25, 2012): 1557–65. http://dx.doi.org/10.1351/pac-con-11-09-27.

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The acyl-Claisen rearrangement, also called a zwitterionic aza-Claisen rearrangement, allows for the synthesis of 2,3-syn-substituted morpholine pent-4-eneamides with high levels of diastereoselectivity. A wide variety of alkyl and aryl substituents can be introduced with yields highly dependent on the stoichiometry of the Lewis acid catalyst. The use of these morpholine amides in the synthesis of the tetrasubstituted tetrahydrofuran lignans fragransin A2, talaumidin, and galbelgin is summarized. The conversion of the Claisen-derived amides into aryl tetraline and 1,1-diarylbutanol lignans via alteration of the protecting groups is also described. Nucleophilic addition of an organometallic reagent to the morpholine amide followed by Wacker oxidation of the alkene gives highly substituted 1,4-diketones, which can be easily converted into fully substituted pyrroles.
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Dissertations / Theses on the topic "Morpholines – chemical synthesis"

1

Bilbeisi, Rana A. 1983. "Expedient synthesis of chiral poly-substituted morpholine and oxazepine derivatives for the preparation of cyclophilin A inhibitors." Thesis, McGill University, 2008. http://digitool.Library.McGill.CA:80/R/?func=dbin-jump-full&object_id=111575.

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An efficient and expedient synthetic method was developed for the preparation of chiral poly-substituted morpholine and oxazepine derivatives. The method was designed in the objective of applying the synthesis to the preparation of Cyclophilin A inhibitors.
The stereo- and regioselective method involves the reaction of enantiopure beta-amino alcohols with alpha,beta-unsaturated aldehydes. The synthesis proceeds through three steps; i) Reductive amination, ii) N-alkylation/ N-tosylation and iii) intramolecular-haloetherification. Stereoselectivity of this last step was controlled by N-alkyl/ N-tosyl groups and substitution across the double bond, and was enhanced by the addition of Bronsted acids. Substitution across the double bond of the starting material controlled the regioselectivity of the method. Morpholines were obtained through 6- exo cyclization and oxazepines were obtained through 7-endo cyclization.
A small library of morpholine-based derivatives was designed in-silico. Affinity and binding modes to the Cyclophilin A were investigated through a docking-based virtual screening study.
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