Synthesis and heteroelectrocyclization of unsymmetrically substituted diazomalonamides / Morzherin YY,Subbotina YO,Nein YI,Kolobov MY,Bakulev VA // RUSSIAN CHEMICAL BULLETIN. - 2004. - V. 53, l. 6. - P. 1305-1310.

ISSN/EISSN:

1066-5285 / нет данных

Type:

Article

Abstract:

A selective procedure was developed for the synthesis of 1,2,3-triazoles and unsymmetrically substituted diazomalonamides. Cyclization of unsymmetrically substituted diazomalonamides to 1,2,3-triazoles was studied by the method of intramolecular competitive reactions. The kinetic and thermodynamic characteristics of the process were determined. Quantum-chemical calculations for the monorotatory electrocyclic and nonrotatory heteroelectrocyclic mechanisms of cyclization were carried out. N-Aryldiazomalonamides undergo cyclization according to the heteroelectrocyclic mechanism, whereas cyclization of N-alkyldiazomalonamides proceeds by the monorotatory mechanism. The experimental constant of competition between these processes is (1.3-8.3) (.) 10(3) (DMSO-d(6)) and (45.2-72.4) (.) 10(3) (CD3OD).

Author keywords:

1,2,3-triazoles; diazo compounds; method of intramolecular competitive reactions; cyclization; quantum-chemical calculations; thermodynamic stability; rate constant DENSITY-FUNCTIONAL THEORY; AB-INITIO; V-TRIAZOLES; MECHANISM; MINDO/3; AM1

DOI:

10.1023/B:RUCB.0000042291.7028

Web of Science ID:

ISI:000224147800026

Соавторы в МНС:

Другие поля

Поле	Значение
Month	JUN
Publisher	CONSULTANTS BUREAU
Address	233 SPRING ST, NEW YORK, NY 10013 USA
Language	English
Keywords-Plus	DENSITY-FUNCTIONAL THEORY; AB-INITIO; V-TRIAZOLES; MECHANISM; MINDO/3; AM1
Research-Areas	Chemistry
Web-of-Science-Categories	Chemistry, Multidisciplinary
Author-Email	morjerine@htf.ustu.ru
ResearcherID-Numbers	Morzherin, Yury/M-7420-2013 Nein, Juliya/P-4340-2016 Subbotina, Julia/L-7131-2016
ORCID-Numbers	Morzherin, Yury/0000-0002-1333-6676 Nein, Juliya/0000-0003-0569-5713 Subbotina, Julia/0000-0002-2227-0787
Number-of-Cited-References	26
Usage-Count-Last-180-days	1
Usage-Count-Since-2013	4
Journal-ISO	Russ. Chem. Bull.
Doc-Delivery-Number	857VR