1966
DOI: 10.1021/ja00973a065
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A New Synthesis of 1,2,4-Oxadiazine Derivatives from 1-Aroylaziridine Oximes

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Cited by 23 publications
(3 citation statements)
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“…1-Aroylaziridine oximes are accessible from aromatic nitrile oxides and aziridines and can rearrange to give the 1,2,4-oxadiazine derivatives (231)(232)(233).…”
Section: Reaction Of Cyanuric Chloride [108-77-0] With Ethyleneimine mentioning
confidence: 99%
“…1-Aroylaziridine oximes are accessible from aromatic nitrile oxides and aziridines and can rearrange to give the 1,2,4-oxadiazine derivatives (231)(232)(233).…”
Section: Reaction Of Cyanuric Chloride [108-77-0] With Ethyleneimine mentioning
confidence: 99%
“…mp 79.5-82O) obtained from column chromatography were recrystallized from a chloroform-hexane solution to give tan crystals of 7, m.p. 80-83'; ir (thin film prepared by evaporation of a benzene solution of 7 on a sodium chloride disk): 1580, 1600, 1625, (2)Aziridinylbenzaldoxime (16a) [22,23].…”
Section: Nov-dec 1986mentioning
confidence: 99%
“…Synthesis of 1,3,4-oxadiazine dicarboxylate from 9-fluorenylmethyl chloroformate Scheme Synthesis of halo carbonyl phenyl carbamates from trifluoromethoxy aniline Scheme Synthesis of Indoxacarb from 1,3,4-oxadiazine dicarboxylate with halo carbonyl phenyl carbamates.Synthesis of oxadiazine scaffolds 1,2,4-oxadiazine scaffoldsSynthesis from 1-arylaziridine oximes 16 which is obtained from benzonitrile oxides with ethyleneimine or propylenimine in an ether, reacting with concentrated HCl by an acid catalyzed mechanism to get intermediate 17 then further basified with NaOH to get the desired scaffold of 1,2,4-oxadiazine 18 (Scheme 6)18 . Synthesis of 1,2,4-oxadiazines from 1-arylaziridine oximes Heating the reaction mixture of nitrone 19 with 1aroylaziridine 20 in toluene and acetic acid to form the corresponding 4-acyltetrahydro-2H-1,2,4oxadiazines 21 with moderate to good yield (Scheme 7)19 .Enantiomeric form of amino alcohol 23 from 1,2,3-trifluoro-5-vinylbenzene 22 which on reacting with carboxylic acid derivative 23A to form an amide 24further undergoes cyclization to form lactam ring 25 then series of conversions to hydroxylamine 26 and cyclization leads to form 1,2,4-oxadiazine enantiomer 27 (Scheme 8) (Yield 90%).…”
mentioning
confidence: 99%