Результаты исследований: Научные публикации в периодических изданиях › статья › Рецензирование
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.
в: Organic and Biomolecular Chemistry, Том 3, № 22, 21.11.2005, стр. 4040-4042.Результаты исследований: Научные публикации в периодических изданиях › статья › Рецензирование
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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