A new strategy for the synthesis of 2-aminobenzimidazol-6-ols via a reaction of quinones with guanidine derivatives is reported. Sequential application of this methodology provided a simple access to the first benzosceptrin analogue bearing a bis-2-aminoimidazole moiety. A concomitant addition of two guanidines to the naphtho[1',2':4,5]imidazo[1,2-a]pyrimidine-5,6-dione, which includes the redox neutral debenzylation and guanidine-assisted cleavage of the 2-aminopyrimidine part resulted in the synthesis of the free challenging contiguous bis-2-aminoimidazole moiety of benzosceprins in one step.
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http://dx.doi.org/10.1021/ol403672p | DOI Listing |
J Org Chem
December 2024
Aix-Marseille Université, CNRS UMR 7325 Centre Interdisciplinaire de Nanoscience de Marseille (CINaM), Campus de Luminy, Marseille cedex 09 13288, France.
The one-pot transamination reactions on a zwitterionic benzoquinonemonoimine yield either a quinoxaline derivative or bis-zwitterionic macrocycles, depending on the number of carbon atoms bridging primary polyamines. These latter products, featuring two confined donor cavities, are the result of a [2 + 2] condensation without the need for template effect or high dilution conditions.
View Article and Find Full Text PDFMethods Protoc
December 2024
Department of Organic and Medicinal Chemistry, Faculty of Pharmacy, University of Pécs, Honvéd Street 1, H-7624 Pécs, Hungary.
An electrochemical investigation of 1,2- and 1,4-dihydroxybenzenes was carried out with platinum macro- and microelectrodes using square wave and cyclic voltammetry techniques. Furthermore, the effect of the two solvents-acetic acid and ethyl acetate-was compared. When using square wave voltammetry, signals only appeared at lower frequencies and only when the supporting electrolyte was in excess, as expected due to the relatively low permittivity of the used solvents.
View Article and Find Full Text PDFOrg Lett
December 2024
Key Laboratory of Photochemical Conversion and Optoelectronic Materials, New Cornerstone Science Laboratory, Technical Institute of Physics and Chemistry, The Chinese Academy of Sciences, Beijing 100190, P. R. China.
Reported herein is the generation of -quinone methides (-QMs) via metal-free visible-light-induced oxidation of -alkylarenols, as well as their subsequent reaction with olefins to afford chromans in good to excellent yields (up to 91%). The key is the selective activation of the benzylic C(sp)-H bond of -alkylarenols via single electron transfer (SET) and the formation of -QMs via hydrogen atom transfer (HAT).
View Article and Find Full Text PDFSci Rep
December 2024
Graduate School of Bioagricultural Sciences, Nagoya University, Nagoya, 464-8601, Japan.
The bioluminescence reaction of firefly luciferase with D-luciferin has become an indispensable imaging technique in modern biology and life science experiments, but the high cost of D-luciferin is limiting its further application. Here, we report a practical, one-pot synthesis of D-luciferin from p-benzoquinone (p-BQ), L-cysteine methyl ester and D-cysteine, with an overall yield of 46%. Our route, which is six steps in length and proceeds via 2-cyano-6-hydroxybenzothiazole, is inspired by the mechanistic study of our previously reported biomimetic, non-enzymatic, one-pot formation of L-luciferin from p-BQ and L-cysteine.
View Article and Find Full Text PDFPharmacol Ther
December 2024
Anesthesia Center for Critical Care Research, Department of Anesthesia, Critical Care and Pain Medicine, Massachusetts General Hospital and Harvard Medical School, Boston, MA 02114, USA. Electronic address:
Hydrogen sulfide (HS) is an environmental hazard well known for its neurotoxicity. In mammalian cells, HS is predominantly generated by transsulfuration pathway enzymes. In addition, HS produced by gut microbiome significantly contributes to the total sulfide burden in the body.
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