A conversion of o-phenylenediamines into benzotriazoles was achieved at room temperature using tert-butyl nitrite. The optimized conditions are also well suited for the transformation of sulfonyl and acyl hydrazines into corresponding azides. This protocol does not require any catalyst or acidic medium. The desired products were obtained in excellent yields in a short span of time.
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http://dx.doi.org/10.1039/c8ob01950a | DOI Listing |
RSC Adv
December 2024
Department of Applied Chemistry, Hanyang University Ansan Gyeonggi-do 15588 Republic of Korea.
The allylation of isochromans at the α-position aerobic DDQ (2,3-dichloro-5,6-dicyano-1,4-benzoquinone) catalysis is described. This process involves the DDQ oxidation of various isochromans under mild conditions to generate oxocarbenium intermediates, which are effectively stabilized in equilibration in the presence of acid before undergoing allylation. Molecular oxygen and -butyl nitrite are employed as an environmentally benign oxidant and mediator, respectively, in the catalytic cycle.
View Article and Find Full Text PDFJ Org Chem
December 2024
Division of Organic Chemistry, CSIR-National Chemical Laboratory, Pune 411008, India.
We report a copper-catalyzed one-pot, multicomponent strategy for the convenient synthesis of -aryl 1,2,3-triazole-1-oxides using arylhydrazines, β-ketoesters, and -butyl nitrite. This mild and simple reaction proceeds in an atom-economic manner with broad substrate scope, affording a variety of -aryl 1,2,3-triazole-1-oxide derivatives. Other salient features of the reaction are good functional group tolerance, scalability, and product diversification.
View Article and Find Full Text PDFBull Exp Biol Med
June 2024
Federal Research Center of Problems of Chemical Physics and Medicinal Chemistry, Russian Academy of Sciences, Chernogolovka, Moscow Region, Russia.
The efficiency of combinations of cytostatics cisplatin and adriamycin with antioxidant sodium 3-(3'-tert-butyl-4-hydroxyphenyl)propyl thiosulfate (TS-13), and nitric oxide (NO) donor NaNO was evaluated on two drug-resistant strains of leukemia P388 with changed redox-status of cells. Simultaneous use of both NO donor and TS-13 in combinations with the cytostatics did not increase the efficiency of therapy. In addition, antioxidant activity of TS-13, NaNO, and their combinations was studied by the method of luminol-dependent chemiluminescence on the model systems with the use of the homogenized cells of sensitive strain and two drug-resistant strains of leukemia P388.
View Article and Find Full Text PDFJ Org Chem
August 2024
Department of Chemistry, University of North Bengal, Darjeeling 734013, India.
Selective installation of halo and nitro groups in heterocyclic backbone through a transition-metal-catalyzed C-H bond activation strategy is immensely alluring to access high-value scaffolds. Here in, we disclosed -pyrimidyl-directed assisted palladium(II)-catalyzed C(sp)8-H halogenation and nitration of substituted 4-quinolone derivatives in the presence of -halosuccinimide and -butyl nitrite, respectively, offering structurally diversified 8-halo/nitro-embedded 4-quinolone frameworks in high yields. Mechanistic studies indicated that the reaction follows an organometallic pathway with a reversible C-H metalation step.
View Article and Find Full Text PDFOrg Biomol Chem
August 2024
State Key Laboratory of New Pharmaceutical Preparations and Excipients, Key Laboratory of Medicinal Chemistry and Molecular Diagnosis of the Ministry of Education, Key Laboratory of Chemical Biology of Hebei Province, College of Chemistry and Materials Science, Hebei Research Center of the Basic Discipline of Synthetic Chemistry, Hebei University, Baoding, Hebei, 071002, P. R. China.
An HO/heating or [bis(trifluoroacetoxy)iodo]benzene promoted radical cascade nitro/azide cyclization of 1-acryloyl-2-cyanoindoles with -butyl nitrite/azidotrimethylsilane was accomplished, which offered a series of nitro/azide-featuring pyrrolo[1,2-]indolediones in good yields. Meanwhile, some scale-up experiments and substituent transformations were performed to test the synthetic value. In addition, the corresponding radical intermediates were successfully detected by HRMS to support the possible reaction pathway.
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