A New Synthesis of 1,2,4-Oxadiazine Derivatives from 1-Aroylaziridine Oximes

Rajagopalan, P.; Talaty, C.N.

doi:10.1021/ja00973a065

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%

Imines, Cyclic

Scherr¹,

Steuerle²,

Fikentscher³

2000

Kirk-Othmer Encyclopedia of Chemical Technology

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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%

Imines, Cyclic

Scherr¹,

Steuerle²,

Fikentscher³

2000

Kirk-Othmer Encyclopedia of Chemical Technology

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“…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%

Syntheses and configurations of some heterocyclic amidoximes. X‐Ray crystal structure of 3‐phenyl‐5,6‐dihydro‐2(1H)‐pyrazinone‐O‐methyloxime

Johnson

Maia

Tan

et al. 1986

Journal of Heterocyclic Chem

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O‐Methyl‐α‐ketophenylacetohydroximoyl chloride (1) was prepared by the reaction of O‐methyl‐α‐methoxyphenylacetohydroximoyl chloride (5) with N‐bromosuccinimide and concentrated hydrobromic acid. Reaction of 1 with ethylenediamine gave 3‐phenyl‐5,6‐dihydro‐2(1H)‐pyrazinone‐O‐methyloxime (6). 3‐Phenyl‐5,6‐cyclohexano‐5,6‐dihydro‐2(1H)‐pyrazininone‐O‐methyloxime (7) was prepared by reaction of 1 with trans‐1,2‐diaminocyclohexane. The X‐ray structure of 6 has been determined. The crystals are orthorhombic, space group Pbca with a = 10.264(3), b = 18.262(4), c = 23.530(4)Å, V = 4411(2)Å3, and Z = 16. The structure, which was refined to R = 0.038 using 1652 observed reflections, shows the amidoxime moiety to be the Z configuration. Reaction of benzohydroximoyl chloride with aziridine gave (Z)‐aziridinylbenzaldoxime (16a). Ultraviolet irradiation of a benzene solution of 16a gave a mixture of the Z and E isomers 16a and 16b. The E isomer 16b underwent thermal isomerization to 16a at 100°. Reaction of 16a with dimethyl sulfate in sodium hydroxide solution gave (Z)‐O‐methylaziridinylbenzaldoxime (17a). Photoisomerization of a hexane solution of 17a gave a mixture of the Z and E isomers 17a and 17b which were separated by preparative glc. The isomers 17a and 17b are resistant to thermal Z = E isomerization. The mechanisms of thermal isomerization of benzamidoximes are discussed.

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“…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%).…”

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confidence: 99%

Review of synthetic strategies in the development of oxadiazine scaffolds

2019

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Heterocycles containing both oxygen and nitrogen are in a tremendous demand for their immense biological activities. Oxadiazines are the scaffolds shown pleasing activities like antibacterial, antifungal, anthelmintic, anti-inflammatory, locomotor, anticonvulsive, antiviral, antitumor, agricultural, insecticidal, nematocidal, miticidal, neurogenerative disorders like Alzheimer disease, blood disorders like anemia and plant regulation. Multiple syntheses of oxadiazine scaffolds like 1,2,4-oxadiazines, 1,2,5-oxadiazines, 1,3,4-oxadiazines, 1,3,5-oxadiazines have been summarized in the review. Several research chemists are making attempts to discover and introduce the new scaffolds for various diseases ailments in the present scenario. Here we made an attempt to introduce the scaffolds of substituted oxadiazines because a lesser amount of research was carried out on these nuclei.

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A New Synthesis of 1,2,4-Oxadiazine Derivatives from 1-Aroylaziridine Oximes

Cited by 23 publications

References 0 publications

Imines, Cyclic

Imines, Cyclic

Syntheses and configurations of some heterocyclic amidoximes. X‐Ray crystal structure of 3‐phenyl‐5,6‐dihydro‐2(1H)‐pyrazinone‐O‐methyloxime

Review of synthetic strategies in the development of oxadiazine scaffolds

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