2015•Russian Journal of Organic ChemistryRequires access

Chemistry of 1,5-diketones: V. Hydrazination of acyclic and heterocyclic (poly)carbonyl compounds

Olga V. Fedotova, Nina V. Pchelintseva, Olga A. Mazhukina, D. N. Ibragimova

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Abstract

Reactions of 2-(1-aryl-3-oxo-3-phenylpropylidene)-3,4-dihydronaphthalen-1(2 H )-ones, 3-(1-aryl-3-oxo-3-phenylpropyl)-3,4-dihydro-2 H -chromene-2,4-diones, and 3,3'-(arylmethylene)bis(3,4-dihydro-2 H -chromene-2,4-diones) with hydrazine hydrate have been studied. Depending on the substrate structure, these reactions involve intramolecular heterocyclization with participation of the exocyclic double bond and sidechain carbonyl group or both oxo groups to give new pyrazole, indazole, and diazepine derivatives, as well as hydrazones.

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What this paper is about

Reactions of 2-(1-aryl-3-oxo-3-phenylpropylidene)-3,4-dihydronaphthalen-1(2 H )-ones, 3-(1-aryl-3-oxo-3-phenylpropyl)-3,4-dihydro-2 H -chromene-2,4-diones, and 3,3'-(arylmethylene)bis(3,4-dihydro-2 H -chromene-2,4-diones) with hydrazine hydrate have been studied. Depending on the substrate structure, these reactions involve intramolecular heterocyclization with participation of the exocyclic double bond and sidechain carbonyl group or both oxo groups to give new pyrazole, indazole, and diazepine derivatives, as well as hydrazones.

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Available abstract

Reactions of 2-(1-aryl-3-oxo-3-phenylpropylidene)-3,4-dihydronaphthalen-1(2 H )-ones, 3-(1-aryl-3-oxo-3-phenylpropyl)-3,4-dihydro-2 H -chromene-2,4-diones, and 3,3'-(arylmethylene)bis(3,4-dihydro-2 H -chromene-2,4-diones) with hydrazine hydrate have been studied. Depending on the substrate structure, these reactions involve intramolecular heterocyclization with participation of the exocyclic double bond and sidechain carbonyl group or both oxo groups to give new pyrazole, indazole, and diazepine derivatives, as well as hydrazones.

Key concepts: Chemistry, Hydrazine (antidepressant), Indazole, Pyrazole, Hydrate, Medicinal chemistry, Diazepine, Aryl

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