628-79-5

Usage

Synthesis Reference(s)

Tetrahedron Letters, 25, p. 263, 1984 DOI: 10.1016/S0040-4039(00)99856-3

Upstream product

• 109-66-0 pentane 
• 110-62-3 pentanal 
• 110-58-7 n-Pentylamine 
• 628-05-7 1-nitropentane 
• 3880-17-9 hexanoic nitrous anhydride 

Downstream Products

• 110-58-7 n-Pentylamine 
• 2050-92-2 Di-n-amylamine 
• 2362-50-7 thianthrene-5-oxide 
• 110-62-3 pentanal 
• 110-59-8 pentanonitrile 
• 90000-41-2 3-Butyl-5-methyl-[1,2,4]oxadiazole 
• 92-85-3 Thianthrene 
• 71-41-0 pentan-1-ol 
• 14633-18-2 (3-butyl-isoxazol-5-yl)-methanol 
• 1239465-20-3 3-butyl-5-methyl-isoxazole-4-carboxylic acid ethyl ester 
• 1315307-38-0 1-(4-fluorophenyl)-3-methoxycarbonyl-5-n-butyl-1,2,4-triazole 
• 1349699-37-1 3-n-butyl-5-(4-methylphenyl)-4,5-dihydroisoxazole 
• 1349699-52-0 3-butyl-5-(4-methylphenyl)-isoxazole 
• 1349699-35-9 5-(4-bromophenyl)-3-n-butyl-4,5-dihydroisoxazole 

Relevant academic research and scientific papers

Exploring Heteroaromatic Rings as a Replacement for the Labile Amide of Antiplasmodial Pantothenamides

Malaria-causing Plasmodium parasites are developing resistance to antimalarial drugs, providing the impetus for new antiplasmodials. Although pantothenamides show potent antiplasmodial activity, hydrolysis by pantetheinases/vanins present in blood rapidly inactivates them. We herein report the facile synthesis and biological activity of a small library of pantothenamide analogues in which the labile amide group is replaced with a heteroaromatic ring. Several of these analogues display nanomolar antiplasmodial activity against Plasmodium falciparum and/or Plasmodium knowlesi, and are stable in the presence of pantetheinase. Both a known triazole and a novel isoxazole derivative were further characterized and found to possess high selectivity indices, medium or high Caco-2 permeability, and medium or low microsomal clearance in vitro. Although they fail to suppress Plasmodium berghei proliferation in vivo, the pharmacokinetic and contact time data presented provide a benchmark for the compound profile likely required to achieve antiplasmodial activity in mice and should facilitate lead optimization.

Some Novel [6-(Isoxazol-5-ylmethoxy)-3-methylbenzofuran-2-yl]phenylmethanone Derivatives, Their Antimicrobial Activity, and Molecular Docking Studies on COVID-19

Abstract: A novel series of benzofuran-isoxazole hybrid heterocyclic unit has been synthesized and their structures characterized by 1H and 13C NMR, and mass spectral data. The synthesized products have been evaluated for their in vitro antibacterial and antifungal activity using Gentamycin sulphate and Nystatin as standard drugs, respectively. Four synthesized products have been determined as highly active against all tested bacterial and fungal strains. Structure–antimicrobial activity relationship has been supported by docking studies of the active compounds against glucosamine-6-phosphate synthase and aspartic proteinase. According to the docking studies, all derivatives exhibit good theoretical affinity with Autodock 4.2 software score in the range of –9.37 and –11.63 kcal/mol against the main protease of COVID-19.

Amidyl Radical Directed Remote Allylation of Unactivated sp3 C?H Bonds by Organic Photoredox Catalysis

The development of visible-light-mediated allylation of unactivated sp3 C?H bonds is reported. The remote allylation was directed by the amidyl radical, which was generated by photocatalytic fragmentation of a pre-functionalized amide precursor. Both aromatic and aliphatic amide derivatives could successfully deliver the remote C?H allylation products in good yields. A variety of electron deficient allyl sulfone systems could be used as δ-carbon radical acceptor.

Stereospecific 1,4-Metallate Shift Enables Stereoconvergent Synthesis of Ketoximes

Reported herein is a stereospecific 1,4-metallate rearrangement for single-geometry ketoxime synthesis from oxime chlorides and arylboronic acids. This strategy exhibits broad substrate scope with excellent stereoselectivity under mild reaction conditions. In comparison with the conventional approaches, each configuration of unsymmetric diaryl oximes, as well as the thermodynamically less stable Z isomer of aryl alkyl ketoximes can be selectively and exclusively obtained. The reactivities of unsymmetric diaryl oximes and the Z isomer of aryl alkyl oximes, a class of underexplored molecules, enables efficient access to the corresponding isoquinolines, isoquinoline N-oxides, and amides having a single configuration.

Rhodium(II)-Catalyzed Formal [3 + 2] Cycloaddition of N-Sulfonyl-1,2,3-triazoles with Isoxazoles: Entry to Polysubstituted 3-Aminopyrroles

A novel rhodium(II)-catalyzed formal [3 + 2] cycloaddition of N-sulfonyl-1,2,3-triazoles with isoxazoles has been achieved that provides an efficient method for the synthesis of polysubstituted 3-aminopyrrole derivatives. An operationally simple one-pot synthesis of the titled compounds from terminal alkynes, tosyl azide, and isoxazoles was also developed. The presented reaction affords an illustrative example of employing 1,2,3-triazoles as the [2C]-component in relevant cycloaddition reactions.

Dual nature of polyethylene glycol under microwave irradiation for the clean synthesis of oximes

Polyethylene glycol (PEG-400 and PEG-600) is an efficient, inexpensive, and recyclable homogeneous medium and catalyst (dual nature) for the clean synthesis of oximes (and aldoximes) under microwave irradiation in the absence of acid and base catalysts. Both aliphatic and aromatic aldehydes/ketones give satisfactory results under microwave irradiation within a short time. Graphical abstract: [Figure not available: see fulltext.]

Ac2O/K2CO3/DMSO: An efficient and practical reagent system for the synthesis of nitriles from aldoximes

The transformation of aldoximes to nitriles using acetic anhydride as dehydration agent under mild reaction conditions is reported. The reaction, which proceeds under weak alkaline condition, allows for the conversion of a range of aldoximes including aromatic aldoximes, alphatic aldoximes, and heterocyclic aldoximes in good to excellent yields. This method has also been successfully applied to the synthesis of calcium channel blocker nilvadipine in pilot scale.

Highly selective oximation of aldehydes by reusable heterogeneous sandwich-type polyoxometalate catalyst

The selectivity of oximation of a variety of aliphatic aldehydes and polycyclic aromatic aldehydes as substrates has been greatly improved by applying a reusable heterogeneous sandwich-type polyoxometalate as catalyst under mild conditions.

Synthesis and antiproliferative evaluation of 3,5-disubstituted 1,2,4-triazoles containing flurophenyl and trifluoromethanephenyl moieties

An efficient 1,3-dipolar cycloaddition method was performed for the synthesis of a series of monofluoro- and trifluoromethane-3,5-disubstituted 1,2,4-triazoles. This efficient cycloaddition method was to react hydrazonoyl hydrochlorides with a series of aldehydes in the presence of NEt3 as catalytic basic agent to provide the corresponding product in 28-94%. Their growth inhibitory results against cancer cells indicated that some of the fluorine- and trifluoromethane-containing compounds could effectively inhibit the growth of NCI-H226 and T-cell leukemia (Jurkat) cells. Among the compounds, trifluoromethane-containing 1,2,4-triazoles possessed the five-membered ring groups on the C-5 position of the triazolic ring, including cyclopentyl, 3-furyl, 3-thienyl, and 2-pyrrolyl, possessed the significant inhibitory activity for NCI-H226 cancer cells.

Transformation of amines to oximes using heterogeneous nanocrystalline titanium(IV) oxide as a green catalyst

The oxidation of amines into corresponding oximes has been described using heterogeneous nanocrystalline titanium(IV) oxide as catalyst and H 2O2 as oxidizing agent in quantitative yields. Both aromatics and aliphatic amines undergo oxidation. Besides this, nanocrystalline TiO2 was recovered and used for further reactions. Hence our present protocol is economical and clean and uses green reagent, solvent, and catalyst. Taylor & Francis Group, LLC.