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Selective transannular ring transformations in azirino-fused eight-membered O,N- Or S,N-heterocycles. / Khlebnikov, Alexander F.; Novikov, Mikhail S.; Shinkevich, Ekaterina Yu; Vidovic, Denis.

In: Organic and Biomolecular Chemistry, Vol. 3, No. 22, 21.11.2005, p. 4040-4042.

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

Harvard

Khlebnikov, AF, Novikov, MS, Shinkevich, EY & Vidovic, D 2005, 'Selective transannular ring transformations in azirino-fused eight-membered O,N- Or S,N-heterocycles', Organic and Biomolecular Chemistry, vol. 3, no. 22, pp. 4040-4042. https://doi.org/10.1039/b512409c

APA

Khlebnikov, A. F., Novikov, M. S., Shinkevich, E. Y., & Vidovic, D. (2005). Selective transannular ring transformations in azirino-fused eight-membered O,N- Or S,N-heterocycles. Organic and Biomolecular Chemistry, 3(22), 4040-4042. https://doi.org/10.1039/b512409c

Vancouver

Khlebnikov AF, Novikov MS, Shinkevich EY, Vidovic D. Selective transannular ring transformations in azirino-fused eight-membered O,N- Or S,N-heterocycles. Organic and Biomolecular Chemistry. 2005 Nov 21;3(22):4040-4042. https://doi.org/10.1039/b512409c

Author

Khlebnikov, Alexander F. ; Novikov, Mikhail S. ; Shinkevich, Ekaterina Yu ; Vidovic, Denis. / Selective transannular ring transformations in azirino-fused eight-membered O,N- Or S,N-heterocycles. In: Organic and Biomolecular Chemistry. 2005 ; Vol. 3, No. 22. pp. 4040-4042.

BibTeX

@article{6f7a3f372d13431b8597fb7e7c4e7431,
title = "Selective transannular ring transformations in azirino-fused eight-membered O,N- Or S,N-heterocycles",
abstract = "The selective transannular ring transformations in azirino-fused eight-membered O,N- or S,N-heterocycles was investigated. The treatment of chlorofluoro-substituted azirinobenzoxazocine initially with anhydrous zinc chloride in methylene chlorine and then with a primary amine in DMSO gave the pyridol[3,2-b][1,4]benzoxacine, and similarly, pyridol[3,2-b][1,4]benzothiazine was obtained from azirinobenzothiazocine. In stong protic acid ring opening of the protonated aziridine occured bytransannular nucleophillic O or S atom. The results show transannular ring transformation in aziro-fused eight-membered O,N- or S,N-hetrocycles involving selective aziridine ring opening and medium size contractions.",
author = "Khlebnikov, {Alexander F.} and Novikov, {Mikhail S.} and Shinkevich, {Ekaterina Yu} and Denis Vidovic",
year = "2005",
month = nov,
day = "21",
doi = "10.1039/b512409c",
language = "English",
volume = "3",
pages = "4040--4042",
journal = "Organic and Biomolecular Chemistry",
issn = "1477-0520",
publisher = "Royal Society of Chemistry",
number = "22",

}

RIS

TY - JOUR

T1 - Selective transannular ring transformations in azirino-fused eight-membered O,N- Or S,N-heterocycles

AU - Khlebnikov, Alexander F.

AU - Novikov, Mikhail S.

AU - Shinkevich, Ekaterina Yu

AU - Vidovic, Denis

PY - 2005/11/21

Y1 - 2005/11/21

N2 - The selective transannular ring transformations in azirino-fused eight-membered O,N- or S,N-heterocycles was investigated. The treatment of chlorofluoro-substituted azirinobenzoxazocine initially with anhydrous zinc chloride in methylene chlorine and then with a primary amine in DMSO gave the pyridol[3,2-b][1,4]benzoxacine, and similarly, pyridol[3,2-b][1,4]benzothiazine was obtained from azirinobenzothiazocine. In stong protic acid ring opening of the protonated aziridine occured bytransannular nucleophillic O or S atom. The results show transannular ring transformation in aziro-fused eight-membered O,N- or S,N-hetrocycles involving selective aziridine ring opening and medium size contractions.

AB - The selective transannular ring transformations in azirino-fused eight-membered O,N- or S,N-heterocycles was investigated. The treatment of chlorofluoro-substituted azirinobenzoxazocine initially with anhydrous zinc chloride in methylene chlorine and then with a primary amine in DMSO gave the pyridol[3,2-b][1,4]benzoxacine, and similarly, pyridol[3,2-b][1,4]benzothiazine was obtained from azirinobenzothiazocine. In stong protic acid ring opening of the protonated aziridine occured bytransannular nucleophillic O or S atom. The results show transannular ring transformation in aziro-fused eight-membered O,N- or S,N-hetrocycles involving selective aziridine ring opening and medium size contractions.

UR - http://www.scopus.com/inward/record.url?scp=28444450567&partnerID=8YFLogxK

U2 - 10.1039/b512409c

DO - 10.1039/b512409c

M3 - Article

AN - SCOPUS:28444450567

VL - 3

SP - 4040

EP - 4042

JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

SN - 1477-0520

IS - 22

ER -

ID: 28249809