New route to 2-cyanobenzimidazoles | Sciact

New route to 2-cyanobenzimidazoles Full article

Journal

Tetrahedron
ISSN: 0040-4020 , E-ISSN: 1464-5416

Output data

Year: 1998, Volume: 54, Number: 33, Pages: 9639-9650 Pages count : 12 DOI: 10.1016/s0040-4020(98)00521-3

Authors

Konstantinova Lidia S. ¹ , Rakitin Oleg A. ¹ , Rees Charles W. ² , Sivadasan Sivaprasad ² , Torroba Tomás ³

Affiliations

1	N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky Prospect, 47, 117913 Moscow, Russia
2	Department of Chemistry, Imperial College of Science, Technology and Medicine, London, UK SW7 2AY
3	Departamento de Química Orgánica, Facultad de Veterinaria, Universidad de Extremadura, E-10071 Cáceres, Spain

N-Monosubstituted 1,2-diaminobenzenes 4 (RMe, Ph, PhCH2, and 3,4-Me2C6H3CH2) react with 4,5-dichloro-1,2,3-dithiazolium chloride 1 in dichloromethane at room temperature to give the corresponding 2-cyanobenzimidazoles 6. If pyridine is added at the beginning of the reaction, the intermediate imino-1,2,3-dithiazoles 5 can be isolated. Upon thermolysis, most of the imines 5 give the 2-cyanobenzimidazoles 6 in fair to good yields. 1,2-Diaminobenzene can be converted in high yield into the mono-imine 5i or the bis-imine 12, RH; thermolysis of 5i gives 2-cyanobenzimidazole in high yield. Conversion of 5 into 6 involves the loss of both sulfur atoms and with the N-phenylimino derivative 5b singlet diatomic sulfur, S2, has been intercepted with norbornene and with 2,3-diphenylbutadiene to give the expected cycloadducts 7 and 8.

Konstantinova L.S. , Rakitin O.A. , Rees C.W. , Sivadasan S. , Torroba T.
New route to 2-cyanobenzimidazoles
Tetrahedron. 1998. V.54. N33. P.9639-9650. DOI: 10.1016/s0040-4020(98)00521-3 WOS Scopus OpenAlex

Web of science:	WOS:000075041900011
Scopus:	2-s2.0-0032514520
OpenAlex:	W2033285948

DB	Citing
OpenAlex	21
Scopus	24
Web of science	21