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2,1,3-benzoselenadiazoles as valuable synthetic intermediates
Södertörn University, Avdelning Naturvetenskap.
2000 (English)In: Current organic chemistry, ISSN 1385-2728, Vol. 4, no 7, 707-726 p.Article in journal (Refereed) Published
Abstract [en]

N-alkyl-1,2-benzenediamines, 4-substituted-3-nitro-1,2-benzenediamines and 3,4-diamino-2-nitrophenols are readily obtained by deselenation of alkyl quaternary salts of 2,1,3-benzoselenadiazoles (bsd) and 5-substituted-4-nitro-bsd. The latter are easily obtained by nitration of 5-X-bsd (X = Me, Br, Cl, F, OMe, NHMe). Nitration of 5-fluoro-bsd yields the 4-nitro derivatives that are accompanied by substantial amounts of the corresponding 4-nitro-bsd-5-ols. ipso-Nitration of 5-fluoro-4-methyl-bsd is followed by instantaneous hydrolysis to (+/-)-4-methyl-4-nitro-bsd-5(4H)-one. Batcho-Leimgruber indole synthesis on 5-methyl-4-nitro-bsd followed by reductive deselenation of 1,2,5-selenadiazolo[3,4-g]indole affords 6,7-diaminoindole. Cyclocondensation of 3-nitro-1,2-benzenediamines with acetylacetone provides a convenient route for the preparation of 2-methyl-4-nitrobenzimidazoles. Less-accessible 6-halo-5-nitro- and 6-methoxy-5-nitroquinoxalines are efficiently synthesized by regioselective condensation of alpha-dicarbonyls with 4-halo- and 4-methoxy-3-nitro-1,2-benzenediamines. The reactive halogen atom or methoxyl group ortho to the nitro substituent renders these quinoxalines versatile intermediates to further heterocycles. The Se-77, C-13 and H-1 NMR chemical shifts of sixteen bsd derivatives, and the C-13 NMR chemical shifts of eight derivatives of 2-methylquinoxalines are presented.

Place, publisher, year, edition, pages
2000. Vol. 4, no 7, 707-726 p.
National Category
Organic Chemistry
URN: urn:nbn:se:sh:diva-15746DOI: 10.2174/1385272003376076ISI: 000088561500003ScopusID: 2-s2.0-0033852736OAI: diva2:508047
Available from: 2012-03-07 Created: 2012-03-07 Last updated: 2014-02-18Bibliographically approved

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