1996
DOI: 10.1002/jhet.5570330606
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Rearrangement reactions of aziridinylbenzaldoximes

Abstract: Reactions of 2,2‐dimethylaziridine with benzohydroximoyl chlorides [ArC(Cl)NOH] give aziridinylbenzaldoximes 1. It has been found that the aziridine ring in these compounds undergoes ring opening in hydrogen chloride‐dioxane solution to give (Z)‐N‐hydroxy‐N′‐(2‐chloro‐2‐methylpropyl)benzenecarboximidamides [ArC(NHCH2CR1R2Cl)NOH, 4]. Treatment of 1 with hydrochloric acid followed by neutralization with aqueous sodium hydroxide gave 6,6‐dimethyl‐3‐aryl‐1,2,4‐oxadiazines 2. Reaction of 4 with sodium hydride in … Show more

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Cited by 17 publications
(9 citation statements)
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“…Oxidation of 4,5-dihydro-1,2,4-oxadiazoles 316 leads to fully conjugated 1,2,4-oxadiazoles 317; the oxidation has been performed with different oxidants such as N-chlorosuccinimide, manganese dioxide, and concentrated HNO 3 (Scheme 13.114) [125,162,169]. …”
Section: Reactions With Nucleophilesmentioning
confidence: 99%
“…Oxidation of 4,5-dihydro-1,2,4-oxadiazoles 316 leads to fully conjugated 1,2,4-oxadiazoles 317; the oxidation has been performed with different oxidants such as N-chlorosuccinimide, manganese dioxide, and concentrated HNO 3 (Scheme 13.114) [125,162,169]. …”
Section: Reactions With Nucleophilesmentioning
confidence: 99%
“…There are other references where the synthesis of substituted 4,5-dihydro-1,2,4-oxadiazoles and their mass spectral data have been reported. These are: (Cavalleri, Bellani, & Lancini, 1973;Grundmenn, Bansal, & Osmanski, 1973;Hussein, 1987;Lessel, 1993Lessel, , 1995Chou et al, 1996;Johnson et al, 1996;Lessel & Herfs, 2000;Aitken et al, 2000).…”
Section: Chemical Ionization Mass Spectrometry Of 45-dihydro-12mentioning
confidence: 97%
“…SCHEME 19. Examination of the electron-impact behavior of 51a-c. Reproduced from the article of Johnson et al (1996), with permission from HeteroCorporation., Copyright 1996.…”
Section: Acknowledgmentsmentioning
confidence: 99%
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