ChemInform Abstract: PHOTOREACTIONS OF PHTHALIMIDE MANNICH BASES IN METHANOL

Roth, H. J.; Schwarz, D.; Hundeshagen, G.

doi:10.1002/chin.197615199

Cited by 2 publications

(3 citation statements)

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“…Of the compounds synthesized, compounds 2, 6-8, and 10 were new, while compounds 1, 3-5, and 9 have been previously reported [16,[27][28][29]. The structures of the synthesized compounds were confirmed by 1 H-and 13 C-NMR (Table 1), UV, IR and MS data ( Table 2).…”

Section: Resultsmentioning

confidence: 70%

Synthesis of 1-Aryl-3-phenethylamino-1-propanone Hydrochlorides as Possible Potent Cytotoxic Agents

2007

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1-Aryl-3-phenethylamino-1-propanone hydrochlorides 1-10, which are potential potent cytotoxic agents, were synthesized via Mannich reactions using paraformaldehyde, phenethylamine hydrochloride as the amine component and acetophenone, 4'-methyl-, 4'-methoxy-, 4'-chloro-, 4'-fluoro-, 4'-bromo-, 2',4'-dichloro-, 4'-nitro-, 4'-hydroxyacetophenone or 2-acetylthiophene as the ketone component. Yields were in the 87-98 % range. Of the compounds synthesized, compounds 2, 6-8 and 10 were new. The optimum reaction conditions were investigated by changing the mol ratios of the reactants, the solvents and the acidity levels using 1 and 10 as representative targets. It was observed that the best mol ratio of the ketone, paraformaldehyde and phenethylamine hydrochloride was 1:1.2:1 (compared with a 2:2.1 ratio), and the most suitable reaction medium was ethanol containing concentrated hydrochloric acid (compared with only ethanol or no solvent). This study may serve as a guide for the conditions of the reactions to synthesize compounds having similar chemical structures.

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Section: Resultsmentioning

confidence: 70%

Synthesis of 1-Aryl-3-phenethylamino-1-propanone Hydrochlorides as Possible Potent Cytotoxic Agents

2007

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“…Rather surprisingly, no photoaddition products are reported in this system. The photochemistry of Mannich bases of phthalimide features largely in the next section, but one interesting report (12) suggests that in some instances photoreduction involving the Mannich base or the parent phthalimide takes place. …”

Section: Photoreduction and Photoadditionmentioning

confidence: 98%

“…Simple N-alkylphthalimides can give benzazepinediones [equation (12)] that arise by way of y-hydrogen transfer and an intermediate fused azetidinol. (t3) This is the major reaction pathway for related alicyclic ami des such as succinimides, glutarimides, or perhydrophthalimides,(l4,16) but in the aromatic imide systems other processes compete effectively.…”

Section: Photoreduction and Photoadditionmentioning

confidence: 99%

Phthalimide and Its Derivatives

Coyle

1984

Synthetic Organic Photochemistry

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ChemInform Abstract: PHOTOREACTIONS OF PHTHALIMIDE MANNICH BASES IN METHANOL

Cited by 2 publications

References 1 publication

Synthesis of 1-Aryl-3-phenethylamino-1-propanone Hydrochlorides as Possible Potent Cytotoxic Agents

Synthesis of 1-Aryl-3-phenethylamino-1-propanone Hydrochlorides as Possible Potent Cytotoxic Agents

Phthalimide and Its Derivatives

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