S-N(H) reactions of pyrazine N-oxides and 1,2,4-triazine 4-oxides with CH-active compounds / Kozhevnikov DN,Kovalev IS,Prokhorov AM,Rusinov VL,Chupakhin ON // RUSSIAN CHEMICAL BULLETIN. - 2003. - V. 52, l. 7. - P. 1588-1594.

ISSN/EISSN:

1066-5285 / нет данных

Type:

Article

Abstract:

Nucleophilic substitution of hydrogen in pyrazine N-oxides under the action of CH-active compounds requires activation with acylating agents. This activation facilitates aromatization of intermediate sigma(H) adducts via elimination of the acid residue to form substituted pyrazines. More electrophilic 1,2.4-triazine 4-oxides react with carbanions derived from CH-active compounds without additional activation according to a scheme, which has previously been unknown for azine N-oxides. This scheme involves aromatization of a H adducts through elimination of water by the E1cb mechanism. The reaction products occur in DMSO-d(6) Solutions predominantly as 6-methylene-1,6-dihydropyrazines and 5-methylene-4,5-dihydro-1,2,4-triazines.

Author keywords:

nucleophilic substitution of hydrogen; 1,2,4-triazine 4-oxide; pyrazine 1-oxide; carbanion; CH-active compounds TERTIARY AMINE OXIDES; NUCLEOPHILIC-SUBSTITUTION; 4-CHLOROQUINOLINE 1-OXIDE; TRIMETHYLSILYL CYANIDE; ACETIC-ANHYDRIDE; HYDROGEN; CYANATION; QUINOLINE; DERIVATIVES; CARBANIONS

DOI:

10.1023/A:1025601311393

Web of Science ID:

ISI:000185987400020

Соавторы в МНС:

Другие поля

Поле	Значение
Month	JUL
Publisher	CONSULTANTS BUREAU
Address	233 SPRING ST, NEW YORK, NY 10013 USA
Language	English
Keywords-Plus	TERTIARY AMINE OXIDES; NUCLEOPHILIC-SUBSTITUTION; 4-CHLOROQUINOLINE 1-OXIDE; TRIMETHYLSILYL CYANIDE; ACETIC-ANHYDRIDE; HYDROGEN; CYANATION; QUINOLINE; DERIVATIVES; CARBANIONS
Research-Areas	Chemistry
Web-of-Science-Categories	Chemistry, Multidisciplinary
ResearcherID-Numbers	Prokhorov, Anton/B-9789-2011
Number-of-Cited-References	30
Usage-Count-Since-2013	5
Journal-ISO	Russ. Chem. Bull.
Doc-Delivery-Number	733ER