THE UTILITY OF MICHAEL CONDENSATION FOR THE SYNTHESIS OF MACROMOLECULE SURFACTANTS FROM AZO-NAPHTHOLS AS POSSIBLE ANTIMICROBIALS

The reactivity of 2-cinnamoyl-5,6,7,8-tetrahydronaphthalene (1) towards MICHAEL condensation with acetylacetone, ethyl acetoacetate, cyclohexanone and malononitrile were studied. Also, the reaction of hydrazine hydrate, phenylhydrazine, hydroxylamine, with 2 were accomplished. Moreover, cyclization of 9 and 11 were performed.

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Synthesis of 2-Cinnamoyl-1,3-indandione Derivatives and their Reactions with Hydrazine, Hydroxylamine Hydrochloride, Thiourea, Secondary Amines and Diethyl Oxalate

Zeitschrift für Naturforschung B ◽

10.1515/znb-1979-0326 ◽

1979 ◽

Vol 34 (3) ◽

pp. 502-506 ◽

Cited By ~ 4

Author(s):

El - Sayed Afsah ◽

Fathy Abdel Kader Amer ◽

Hassan Etman

Keyword(s):

Ethyl Acetoacetate ◽

Polyphosphoric Acid ◽

Hydroxylamine Hydrochloride ◽

Secondary Amines ◽

Molar Ratio ◽

Diethyl Oxalate ◽

Acetyl Acetone ◽

Michael Condensation ◽

Dibromo Derivative

AbstractA series of 2-cinnamoyl-1,3-indandiones (2a-e) were obtained by condensing 1 with aldehydes. Treatment of 2 a with hydrazine or hydroxylamine hydrochloride gave 2-(5-phenyl-2-pyrazolinyl or -isoxazolinyl)-1,3-indandione (3 and 5) respectively, and when treated with thiourea gave 2-(6-phenyl-2-thioxo-4-pyrimidinyl)-1,3-indandione (6).The formation of 2-(β-piperidino-, -morpholino- and -arylmercaptohydrocinnamoyl)- 1,3-indandiones (7a-b and 8a-b) from 2 a was investigated. Compound 7b when treated with hydrazine gave 9. The 2-(α, β-dimorpholinohydrocinnamoyl) derivative (11) was obtained by the action of morpholine on the dibromo derivative (10). The Michael condensation of 2a with ethyl acetoacetate or acetyl acetone was investigated. Treatment of 1 with benzaldehyde in (3:1) molar ratio gave 14, which reacted with diethyl oxalate to give 15. Cyclization of 15 with polyphosphoric acid lead to the formation of 16.

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Diastereoselective multi-component tandem condensation: synthesis of 2-amino-4-(2-furanone)-4H-chromene-3-carbonitriles

Organic & Biomolecular Chemistry ◽

10.1039/c9ob01345h ◽

2019 ◽

Vol 17 (39) ◽

pp. 8853-8857 ◽

Cited By ~ 3

Author(s):

Vijay Gupta ◽

Debashish Sahu ◽

Shailja Jain ◽

Kumar Vanka ◽

Ravi P. Singh

Keyword(s):

Reaction Proceeds ◽

Michael Condensation ◽

Three Components

Highly syn-selective unification of three components (salicylaldehyde, malononitrile and butenolides) in the presence of sodium tert-butoxide has been realised. The reaction proceeds via a tandem Knoevenagel/Pinner/vinylogous Michael condensation.

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