Nucleophilic ring-opening of the azole and azine moieties in 6-nitro-1,2,4-triazolo{[}1,5-a]pyrimidin-7-ones / Ulomsky EN,Voronin VV,Rusinov VL,Chupakhin ON // RUSSIAN CHEMICAL BULLETIN. - 2001. - V. 50, l. 4. - P. 682-688.

ISSN/EISSN:

1066-5285 / нет данных

Type:

Article

Abstract:

The effects of the nature of the nucleophile and the structure of 6-nitrotriazolo{[}1,5-alpyrimidinones on the direction of the ring opening were investigated. The triazole ring is opened under the action of strong bases, such as alkoxides or alkalis, to form 2-cyanoamino-pyrimidinones and then 2-aminopyrimidinones. The results of the reactions with N-nucleophiles depend on the accessibility of position 5 of the heterocycle. Thus, sterically hindered secondary amines react with 5-methyltriazolopyrimidinones to give 2-guanidinopyrimidinones and then 2-aminopyrimidinones. In the absence of a substituent at position 5, the azine ring is opened to form 4-alkyl-3-amino-1,2,4-triazoles and 3-amino-2-nitroacrylamides. Under the action of primary amines, only the pyrimidine fragment is cleaved.

Author keywords:

6-nitro-1,2,4-triazolo{[}1,5-a]pyrimidin-7-ones; 3-amino-1,2,4-triazoles; 3-amino-2-nitrocrotonamide; 3-amino-2-nitroacrylamides; N-alkyl-N-hetarylcyanamides; 2-alkylamino-4-methyl-5-nitropyrimidin-7- NITROAZINES

DOI:

10.1023/A:1011373131012

Web of Science ID:

ISI:000170448600021

Соавторы в МНС:

Другие поля

Поле	Значение
Month	APR
Publisher	CONSULTANTS BUREAU
Address	233 SPRING ST, NEW YORK, NY 10013 USA
Language	English
Keywords-Plus	NITROAZINES
Research-Areas	Chemistry
Web-of-Science-Categories	Chemistry, Multidisciplinary
Number-of-Cited-References	11
Usage-Count-Since-2013	2
Journal-ISO	Russ. Chem. Bull.
Doc-Delivery-Number	462YU