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Molecular diversity of TEMPO-mediated cycloaddition of ketohydrazones and 3-phenacylideneoxindoles.
- Source :
-
New Journal of Chemistry . 3/21/2021, Vol. 45 Issue 11, p5075-5080. 6p. - Publication Year :
- 2021
-
Abstract
- TEMPO promoted cycloaddition reaction of different kinds of ketohydrazones or aldohydrazones with 3-phenacylideneoxindoles showed very interesting molecular diversity according to the chemical structures and reaction conditions. The reactions with 1-(3,4-dihydronaphthalen-1-ylidene)-2-arylhydrazines or 1-cyclohexylidene-2-arylhydrazines in acetonitrile at 80 °C afforded functionalized spiro[benzo[h]cinnoline-3,3′-indolines] or spiro[cinnoline-3,3′-indolines] via aza-Diels–Alder reaction of the in situ generated 1,2-diaza-1,3-diene. The reactions with 2-(2-phenylethylidene)-1-arylhydrazines in dioxane afforded functionalized spiro[indoline-3,3′-pyrazoles] though a [3+2] cycloaddition reaction of the in situ generated 1,3-dipolar azomethine imine. On the other hand, a similar reaction in acetonitrile unusually resulted in pyrazole derivatives via sequential [3+2] cycloaddition and a ring-opening process. [ABSTRACT FROM AUTHOR]
Details
- Language :
- English
- ISSN :
- 11440546
- Volume :
- 45
- Issue :
- 11
- Database :
- Academic Search Index
- Journal :
- New Journal of Chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 149410475
- Full Text :
- https://doi.org/10.1039/d0nj06036d