Facile selective synthesis of 2-methyl-5-amino-1,2,4-oxadiazolium bromides as further targets for nucleophilic additions

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Facile selective synthesis of 2-methyl-5-amino-1,2,4-oxadiazolium bromides as further targets for nucleophilic additions. / Il'In, Mikhail V.; Bolotin, Dmitrii S.; Suslonov, Vitalii V.; Kukushkin, Vadim Yu.

In: New Journal of Chemistry, Vol. 42, No. 12, 01.01.2018, p. 9373-9376.

Research output: Contribution to journal › Article › peer-review

BibTeX

@article{bcc52e770b964c5a9f42aceb00626c75,

title = "Facile selective synthesis of 2-methyl-5-amino-1,2,4-oxadiazolium bromides as further targets for nucleophilic additions",

abstract = "The reaction of aminonitrones R1C(NH2) = N+(Me)O- (R1 = Alk, Ar) with isocyanides R2NC (R2 = Alk, Ar; 1.2 equiv.) and Br2 (1 equiv.) conducted in CHCl3 (RT, 5 min) gives 2-methyl-5-amino-1,2,4-oxadiazolium bromides in good to excellent yields (65-95%; 16 examples). These species are highly electrophilically activated and 5-cyclohexylamino-2-methyl-3-phenyl-1,2,4-oxadiazolium bromide, taken as a model compound for the reactivity study, reacts rapidly under mild conditions with hydroxylamine, hydrazine, or benzamidine, to give 5-cyclohexylamino-3-phenyl-1,2,4-oxadiazole (88%), 5-cyclohexylamino-3-phenyl-1,2,4-triazole (95%), and 2-cyclohexylamino-4,6-diphenyl-1,3,5-triazine (64%), respectively. Treatment of the oxadiazolium salt with excess water provides N-benzoyl-N′-cyclohexylurea (95%).",

author = "Il'In, {Mikhail V.} and Bolotin, {Dmitrii S.} and Suslonov, {Vitalii V.} and Kukushkin, {Vadim Yu}",

year = "2018",

month = jan,

day = "1",

doi = "10.1039/c8nj01682h",

language = "English",

volume = "42",

pages = "9373--9376",

journal = "New Journal of Chemistry",

issn = "1144-0546",

publisher = "Royal Society of Chemistry",

number = "12",

}

RIS

TY - JOUR

T1 - Facile selective synthesis of 2-methyl-5-amino-1,2,4-oxadiazolium bromides as further targets for nucleophilic additions

AU - Il'In, Mikhail V.

AU - Bolotin, Dmitrii S.

AU - Suslonov, Vitalii V.

AU - Kukushkin, Vadim Yu

PY - 2018/1/1

Y1 - 2018/1/1

N2 - The reaction of aminonitrones R1C(NH2) = N+(Me)O- (R1 = Alk, Ar) with isocyanides R2NC (R2 = Alk, Ar; 1.2 equiv.) and Br2 (1 equiv.) conducted in CHCl3 (RT, 5 min) gives 2-methyl-5-amino-1,2,4-oxadiazolium bromides in good to excellent yields (65-95%; 16 examples). These species are highly electrophilically activated and 5-cyclohexylamino-2-methyl-3-phenyl-1,2,4-oxadiazolium bromide, taken as a model compound for the reactivity study, reacts rapidly under mild conditions with hydroxylamine, hydrazine, or benzamidine, to give 5-cyclohexylamino-3-phenyl-1,2,4-oxadiazole (88%), 5-cyclohexylamino-3-phenyl-1,2,4-triazole (95%), and 2-cyclohexylamino-4,6-diphenyl-1,3,5-triazine (64%), respectively. Treatment of the oxadiazolium salt with excess water provides N-benzoyl-N′-cyclohexylurea (95%).

AB - The reaction of aminonitrones R1C(NH2) = N+(Me)O- (R1 = Alk, Ar) with isocyanides R2NC (R2 = Alk, Ar; 1.2 equiv.) and Br2 (1 equiv.) conducted in CHCl3 (RT, 5 min) gives 2-methyl-5-amino-1,2,4-oxadiazolium bromides in good to excellent yields (65-95%; 16 examples). These species are highly electrophilically activated and 5-cyclohexylamino-2-methyl-3-phenyl-1,2,4-oxadiazolium bromide, taken as a model compound for the reactivity study, reacts rapidly under mild conditions with hydroxylamine, hydrazine, or benzamidine, to give 5-cyclohexylamino-3-phenyl-1,2,4-oxadiazole (88%), 5-cyclohexylamino-3-phenyl-1,2,4-triazole (95%), and 2-cyclohexylamino-4,6-diphenyl-1,3,5-triazine (64%), respectively. Treatment of the oxadiazolium salt with excess water provides N-benzoyl-N′-cyclohexylurea (95%).

UR - http://www.scopus.com/inward/record.url?scp=85048419570&partnerID=8YFLogxK

U2 - 10.1039/c8nj01682h

DO - 10.1039/c8nj01682h

M3 - Article

AN - SCOPUS:85048419570

VL - 42

SP - 9373

EP - 9376

JO - New Journal of Chemistry

JF - New Journal of Chemistry

SN - 1144-0546

IS - 12

ER -

ID: 41787233