H-1- and C-13-NMR investigations on sigma-adduct formation of 1,2,4-triazine 4-oxides and 3-chloro-6-phenyl-1,2,4-triazine with liquid ammonia and alkylamines / Rykowski A,Chupakhin ON,Kozhevnikov DN,Kozhevnikov VN,Rusinov VL,Van der Plas HC // HETEROCYCLES. - 2001. - V. 55, l. 1. - P. 127-133.

ISSN/EISSN:

0385-5414 / нет данных

Type:

Article

Abstract:

H-1- and C-13-NMR spectra of the sigma -adducts formed between 6-phenyl-1,2,4-triazine 4-oxide (la), 3-ethyl-6-phenyl-1,2,4-triazine 4-oxide (Ib) and liquid ammonia, methylamine or dimethylamine are described, together with H-1 NMR spectra of 3-chloro-6-phenyl-1,2,4-triazine (7) in liquid ammonia. The results of the NMR study have shown that the carbon C-5 in 1a-b and 7 is the preferred site for nucleophilic attack by liquid ammonia and alkylamines at low temperatures (from -75 degrees to -20 degreesC). The sigma -adduct (5e) formed between la and dimethylamine at -75 degreesC on heating to -20 degreesC irreversibly converts to open-chain product (3a), via intermediary C-3 sigma -adduct (6). The amination of 7 into 3-amino-6-phenyl-1,2,4-triazine (10) occurs via S-N(AE) mechanism involving the isomerisation of the C-5 sigma -adduct (8) into the C-3 sigma -adduct (9) as confirmed by a N-15 study with labeled liquid ammonia.

Author keywords:

POTASSIUM-PERMANGANATE; CHICHIBABIN AMINATION; REAGENT

DOI:

нет данных

Web of Science ID:

ISI:000167581900016

Соавторы в МНС:

Другие поля

Поле	Значение
Month	JAN 1
Publisher	PERGAMON-ELSEVIER SCIENCE LTD
Address	THE BOULEVARD, LANGFORD LANE, KIDLINGTON, OXFORD OX5 1GB, ENGLAND
Language	English
Keywords-Plus	POTASSIUM-PERMANGANATE; CHICHIBABIN AMINATION; REAGENT
Research-Areas	Chemistry
Web-of-Science-Categories	Chemistry, Organic
ResearcherID-Numbers	Kozhevnikov, Valery/B-1178-2010
ORCID-Numbers	Kozhevnikov, Valery/0000-0001-7032-8886
Number-of-Cited-References	8
Usage-Count-Last-180-days	1
Usage-Count-Since-2013	3
Journal-ISO	Heterocycles
Doc-Delivery-Number	412YF