- Investigation of Masked N-Acyl-N-isocyanates: Support for Oxadiazolones as Blocked N-Isocyanate Precursors
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In contrast to carbon-substituted isocyanates that are common building blocks, N-substituted isocyanates remain underdeveloped and reports on their N-acyl derivatives (i. e. amido-isocyanates) are exceedingly rare. Herein, amido-isocyanates were investiga
- Gagné-Monfette, William,Vincent-Rocan, Jean-Fran?ois,Lutes, Owen C.,O'Keefe, Geneviève F.,Jeanneret, Alexandria D. M.,Blanger, Claire,Ivanovich, Ryan A.,Beauchemin, André M.
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supporting information
p. 14051 - 14056
(2021/09/14)
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- Application of N-Acylbenzotriazoles in the Synthesis of 5-Substituted 2-Ethoxy-1,3,4-oxadiazoles as Building Blocks toward 3,5-Disubstituted 1,3,4-Oxadiazol-2(3H)-ones
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5-Substituted-2-ethoxy-1,3,4-oxadiazoles were conveniently prepared through a one-pot sequential N-acylation/dehydrative cyclization between ethyl carbazate and N-acylbenzotriazoles in the presence of Ph3P-I2 as a dehydrating agent. Subsequent treatment with a stoichiometric amount of alkyl halides (X = Cl, Br, I) enables a rapid access to a variety of 3,5-disubstituted 1,3,4-oxadiazol-2(3H)-ones in good to excellent yields.
- Wet-Osot, Sirawit,Phakhodee, Wong,Pattarawarapan, Mookda
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p. 9923 - 9929
(2017/09/23)
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- I2 mediated synthesis of 5-substituted-3-methyl/benzyl-1,3,4-oxadiazol-2(3H)-ones via sequential condensation/oxidative cyclization and rearrangement
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A simple and efficient iodine-assisted protocol for the synthesis of 5-substituted-3-methyl/benzyl-1,3,4-oxadiazol-2(3H)-ones has been developed. The reaction involves a sequential condensation followed by tandem oxidative cyclization and rearrangement of
- Patel, Shyam Sunder,Chandna, Nisha,Kumar, Shreemoyee,Jain, Nidhi
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p. 5683 - 5689
(2016/07/06)
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- The use of a Mitsunobu reagent for the formation of heterocycles: A simple method for the preparation of 3-alkyl-5-aryl-1,3,4-oxadiazol-2(3H)-ones from carboxylic acids
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The reaction of carboxylic acids with Mitsunobu reagents, prepared by the reaction of triphenylphosphine with dialkyl azodicarboxylates, followed by heating at 180-190 °C under solvent-free conditions, afforded 3-alkyl-5-aryl-1,3,4-oxadiazol-2(3H)-ones. This facile and convenient method readily provides the 1,3,4-oxadiazolone ring systems in good yields using a one-pot protocol starting from the corresponding carboxylic acids. It was also demonstrated that the presence of a catalytic base facilitates the final ring closure forming the 1,3,4-oxadiazol-2(3H)-one.
- Sugimoto, Osamu,Arakaki, Tomoyo,Kamio, Hiroka,Tanji, Ken-Ichi
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supporting information
p. 7314 - 7317
(2014/07/07)
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- Propylene oxide assisted one-pot, tandem synthesis of substituted-1,3,4- oxadiazole-2(3H)-ones in water
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It has been developed for the synthesis of substituted-1,3,4-oxadiazole- 2(3H)-one derivatives via a novel one-pot, tandem procedure assisted by propylene oxide. The 5-substitued-1,3,4-oxadiazole-2(3H)-ones and 3,5-disubstitued-1,3,4-oxadiazole-2(3H)-ones were, respectively, obtained from three-component reaction of acylhydrazines, carbon disulfide, and propylene oxide, and four-component reaction of acylhydarazines, carbon disulfide, propylene oxide, and organic halides. The reactions were carried out using water as solvent in the presence of potassium phosphate to afford the expected products in good to excellent yields.
- Yan, Xu,Zhou, Shuo,Wang, Yuanqiang,Ge, Zemei,Cheng, Tieming,Li, Runtao
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p. 7978 - 7983
(2012/09/21)
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- Verdazyl radicals as substrates for organic synthesis: A synthesis of 3-methyl-5-aryl-1,3,4-oxadiazolones
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The synthesis of oxadiazolones under hydrolytic conditions is described for a series of 3-methyl-5-aryl-1,3,4-oxadiazolone compounds. The unique starting materials for the hydrolysis reaction are obtained from efficient 1,3-dipolar cycloaddition reactions
- Bancerz, Matthew,Georges, Michael K.
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p. 6377 - 6382
(2011/10/05)
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- Design, synthesis and evaluation of D,D-peptidase and beta-lactamase inhibitors: Azapeptides, oxapeptides and related heterocycles
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Reactive molecules susceptible to form stable acyl enzyme intermediates with D,D-peptidases and β-lactamases were designed as potential irreversible inhibitors of Penicillin Sensitive Enzymes (PSEs). The structures examined were a series of azapeptides and oxapeptides, both analogs of the D-Ala-D-Ala substrate, and some heterocycles, such as imidazolidinones and oxazolidinones, both analogs of the β-lactam antibiotics. The various strategies investigated for their synthesis are described and discussed. Some biological results are reported.
- Marchand-Brynaert,Mougenot,Combret,Belotti,Guillot,Ghosez
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p. 455 - 469
(2007/10/02)
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- Reaction of Oxalyl and Malonyl Chloride with 1,1-Dimethyl-2-substituted Hydrazides
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Recently we reported the reaction of 1,1-dimethyl-4-substituted semicarbazides with phosgene to occur with formation of several new heterocyclic ring systems.Here we report the reaction of several semicarbazides, thiosemicarbazides and related acyl substi
- Sarker, S. R.,Stone, D. M.,Evain, E. J.,Cooley, J. H.,Scott, B. L.,Willett, R. D.
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p. 1535 - 1540
(2007/10/02)
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- Syntheses and thermal rearrangements of 2-phenyl-4-alkoxycarbonyl-1,3,4-oxadiazol-5(4H)-ones and related sulfur compounds
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Syntheses of nine 2-phenyl-4-alkoxycarbonyl-1,3,4-oxadiazol-5(4H)-ones are described.On heating about 200 deg C, these compounds decarboxylate and give 2-phenyl-4-alkyl-1,3,4-oxadiazol-5(4H)-ones.Although many analogies suggest that the rearrangement proceeds through the cyclisation of a 1,5-dipole, arising from the decarboxylation of the heterocycle, no direct evidence for such a mechanism was obtained.On the contrary, the synthesis and the thermal rearrangement of four related sulfur compounds show that such a postulated intermediate cannot explain all the experimental results.
- Golfier, M.,Guillerez, M. G.
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- Synthesis of 5-Aryl-3-carbazoyl-1,3,4-oxadiazol-2(3H)-one. Derivatives and their Ring Transformation into 5-Benzamido-1,2,4-triazolidine-3,5-dione Derivatives
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Some 5-aryl-3-carbazoyl-1,3,4-oxadiazol-2(3H)-one derivatives 6 and 9 have been synthesized in two ways.The expected thermal ring transformation into 2,5-disubstituted 1,3,4-oxadiazoles did not occur but, by acid hydrolysis of 5-aryl-3-3-benzylidene-2-me
- Milcent, Rene,Barbier, Geo,Tzirenstchikow, Tatiana,Lebreton, Luc
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p. 231 - 236
(2007/10/02)
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- Heterocyclic Photorearrangements. Photochemical Behaviour of Some 3,5-Disubstituted 1,2,4-Oxadiazoles in Methanol at 254 nm
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Photochemical behaviour of some 3,5-disubstituted 1,2,4-oxadiazoles in methanol at 254 nm has been investigated.Ring photoisomerization to the 1,3,4-oxadiazole heterocycle or formation of open chain compounds involving the nucleophilic solvent was shown to depend on the nature and the position of the substituent.Photoinduced ring closure into the benzimidazole system, involving a 3-N-phenylamino side chain sequence and a photolytic intermediate of the oxadiazole heterocycle, is also reported.
- Buscemi, Silvestre,Cicero, Maria G.,Vivona, Nicolo,Caronna, Tullio
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p. 931 - 935
(2007/10/02)
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- PHOTOREAKTIONEN DES 3-METHYL-4-PHENYLSYDNONS
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A procedure for the synthesis of 3-methyl-4-phenylsydnone (1) is given.UV. irradiation of 1 in solution generates the nitrile-imine 4 which reacts with activated C,C double bonds and with heterocumulenes to give five-membered heterocycles.In contrast to the 2H-azirines which photochemically react with the C,O double bond of phenylisocyanate, 4 adds to the C,N double bond of the latter.
- Pfoertner, Karl-Heinz,Foricher, Joseph
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p. 653 - 657
(2007/10/02)
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