Synthesis of 3-substituted 1-aryl-4,6-dinitro-1H-indazoles based on picrylacetaldehyde and their behavior in nucleophilic substitution reactions Full article
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Russian Chemical Bulletin
ISSN: 1573-9171 , E-ISSN: 1066-5285 |
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| Output data | Year: 2003, Volume: 52, Number: 8, Pages: 1782-1790 Pages count : 9 DOI: 10.1023/a:1026008821698 | ||
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Abstract:
A method for the synthesis of 1-aryl-3-formyl-4,6-dinitro-1H-indazoles by the reaction of picrylacetaldehyde with aryldiazonium salts followed by intramolecular cyclization of the resulting picrylglyoxal monoarylhydrazones was developed. Various 4,6-dinitro-1-phenyl-1H-indazoles substituted in position 3 were prepared via transformations involving the formyl group of 3-formyl-4,6-dinitro-1-phenyl-1H-indazole. 3-R-4,6-Dinitro-1-phenyl-1H-indazoles (R = CHO, CN, 1,3-dioxolan-2-yl) react regiospecifically with anionic O-, S-, and N-nucleophiles, in particular, with replacement of only the 4-NO2 group. Thus previously unknown 3-R-4-Nu-6-nitro-1-phenyl-1H-indazoles were synthesized (Nu is a nucleophile residue).
Cite:
Starosotnikov A.M.
, Kachala V.V.
, Lobach A.V.
, Vinogradov V.M.
, Shevelev S.A.
Synthesis of 3-substituted 1-aryl-4,6-dinitro-1H-indazoles based on picrylacetaldehyde and their behavior in nucleophilic substitution reactions
Russian Chemical Bulletin. 2003. V.52. N8. P.1782-1790. DOI: 10.1023/a:1026008821698 WOS Scopus OpenAlex
Synthesis of 3-substituted 1-aryl-4,6-dinitro-1H-indazoles based on picrylacetaldehyde and their behavior in nucleophilic substitution reactions
Russian Chemical Bulletin. 2003. V.52. N8. P.1782-1790. DOI: 10.1023/a:1026008821698 WOS Scopus OpenAlex
Identifiers:
| Web of science: | WOS:000186446500020 |
| Scopus: | 2-s2.0-0345742318 |
| OpenAlex: | W2950045212 |