Synthesis of 4-arylcarbamoyl-5-(2-hydroxynaphthylazo)imidazoles and 1-substituted naphtho[2,1-e]imidazo[5,1-c][1,2,4]triazines / Sadchikova E.V., Mokrushin V.S. // Russian Chemical Bulletin. - 2006. - V. 55, l. 7. - P. 1255-1261.

ISSN:

10665285

Type:

Article

Abstract:

The reactions of β-naphthol with 5-diazoimidazoles and imidazolyl-5-diazonium salts containing chemically different carboxamide groups in position 4 were studied. Heterocyclization of 4-arylcarbamoyl-5-(2- hydroxynaphthylazo)imidazoles formed in these reactions was investigated. The presence of the NH fragment in the amide group prevents this process, the reaction giving instead 3-substituted 3,7-dihydroimidazo[4,5-d][1,2,3]triazin-4- ones, which is due to reversibility of C-azo coupling. Methods for modification of 1-ethoxycarbonyl group in the naphtho[2,1-e]imidazo[5,1-c][1,2,4]triazine system were developed and used to prepare substituted carboxamides inaccessible by other routes. © Springer Science+Business Media, Inc. 2006.

Author keywords:

5-diazoimidazoles; 5-imidazolyldiazonium salts; Azo compounds; C-azo coupling; Naphtho[2,1-e]imidazo[5,1-c][1,2,4]triazines; Reactivity

Index keywords:

нет данных

DOI:

10.1007/s11172-006-0408-7

Смотреть в Scopus:

https://www.scopus.com/inward/record.uri?eid=2-s2.0-33751567566&doi=10.1007%2fs11172-006-0408-7&partnerID=40&md5=9314251a931c585c73f76c6c1de37b32

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Поле	Значение
Link	https://www.scopus.com/inward/record.uri?eid=2-s2.0-33751567566&doi=10.1007%2fs11172-006-0408-7&partnerID=40&md5=9314251a931c585c73f76c6c1de37b32
Affiliations	Ural State Technical University - UPI, 19 ul. Mira, 620002 Ekaterinburg, Russian Federation
Author Keywords	5-diazoimidazoles; 5-imidazolyldiazonium salts; Azo compounds; C-azo coupling; Naphtho[2,1-e]imidazo[5,1-c][1,2,4]triazines; Reactivity
References	Vilarrassa, J., Granados, R., (1974) J. Heterocycl. Chem., 11, p. 867; Castillun, S., Melindez, E., (1982) J. Heterocycl. Chem., 19, p. 61; Horton, J.K., Stevens, M.F.G., (1981) J. Chem. Soc., Perkin Trans. 1, p. 1433; Sadchikova, E.V., Mokrushin, V.S., (2005) Izv. Akad. Nauk. Ser. Khim., p. 348; (2005) Buss. Chem. Bull., Int. Ed., 54, p. 354; Mokrushin, V.S., Bezmaternikh, M.A., (1998) Mendeleev Commun., p. 197; Bezmaternykh, M.A., Mokrushin, V.S., Sadchikova, E.V., (2000) Khimiya Geterotsikl. Soedinen., p. 540; (2000) Chem. Heterocycl. Compd., p. 394. , Engl. Transl; Langnel, D.A.F., Arrowsmith, J., Stevens, M.F.G., (2000) Arkivoc, 1, p. 421; Sadchikova, E.V., Mokrushin, V.S., (2003) Izv. Akad. Nauk. Ser. Khim., p. 1516; (2003) Russ. Chem. Bull., Int. Ed., 52, p. 1600
Correspondence Address	Sadchikova, E.V.; Ural State Technical University - UPI, 19 ul. Mira, 620002 Ekaterinburg, Russian Federation; email: selena@htf.ustu.ru
Language of Original Document	English
Abbreviated Source Title	Russ. Chem. Bull.
Source	Scopus