Die Bestrahlung von Bis-phthalimidomethyl-alkylaminen in Aceton fuhrt hauptsachlich zu einfachen und doppelten Ringschlussen unter Bildung von tricyclischen, kondensierten Imidazollidinen und hexacyclischen, kondensierten Imidazolidino-imidazolidinen.



Photoreactions of Bis-phthalimidomethyl-alkylamines



Irradiation of bis-phthalimidomethyl-alkylamines in acetone leads mainly to ring closures and double ring closures. Tricyclic, condensed imidazolidines and hexacyclic, condensed imidazolidino-imidazolidines are obtained.

Photoreaktionen von Bis-phthalimidomethyl-alkylaminen

Further advances in the chemistry of mannich bases

Photoreactions of cyclic imides. Examples of synthetic organic photochemistry

Organic carbonyl compounds featured prominently in the early period of mushrooming growth in the field of organic photochemistry. Initially much attention was focused on the photoreactions of ketones and, to a lesser extent, aldehydes. Subsequently carboxylic acids and their derivatives were investigated more extensively, and reviews of their photochemistry show a wide range of interesting reactions.(1,2) Cyclic carboximides have emerged as showing a considerable variety of photochemical behavior, and many of the reactions can be put to good use in the synthesis of heterocyclic compounds. Reactions of the hydrogen abstraction/cyclization type have been reviewed by the director of the most active research group in this area,(3) and a more comprehensive review of imide photochemistry is available.(4) The purpose of this chapter is to describe the photochemical reactions of aromatic imides related to phthalimide, and to emphasize the synthetic applications of the processes. At various points in the discussion the main parallels and differences between aromatic and aliphatic imides will also be covered briefly.

Phthalimide and Its Derivatives

Durch Kondensation von Aryl-alkyl-keton-Mannichbasen mit dem primaren Enamin des Acetylacetons entstehen 3-Acetylpyridine.



Die Kondensation mit den Enaminen des Dihydroresorcins und des Dimedons fuhrt zu 1,4,5,6,7,8-Hexahydrochinolin-5-onen, die leicht zu 5,6,7,8-Tetrahydrochinolin-5-onen dehydriert werden.



Synthesis of Pharmacologically Active Heterocyclic Compounds via Mannich Reaction, I. 3-Acetylpyridines and Hydroquinolines



3-Acetylpyridines are obtained by condensation of ketone Mannich bases with the enamine of acetylacetone.



1.4.5.6.7.8-Hexahydroquinolin-5-ones and 5.6.7.8-tetrahydroquinolin-5-ones are obtained by condensation of ketone Mannich bases with the enamines of dihydroresorcinol or dimedone and subsequent dehydrogenation.

Versuche zur Synthese pharmakologisch wirksamer Heterocyclen via Mannich-Reaktion, I. 3-Acetylpyridine und partiell hydrierte Chinoline†

Die Bestrahlung von Phthalimid in einem, Gemisch von Dioxan und Aceton fuhrt zu den Photoprodukten 1 bis 4; in Isopropanol entstehen 2 bis 4; in Athanol 2, 3 und 5; in Methanol 2 und 3.



Photoreactions of Phthalimide



Irradiation of phthalimide in a mixture of dioxane and acetone leads to the photo compounds 1, 2, 3 and 4; in isopropanol 2, 3 and 4, in ethanol 2, 3 and 5, in methanol 2 and 3 are produced.

Photoreaktionen von Bis-phthalimidomethyl-alkylaminen

Citations

Further advances in the chemistry of mannich bases

Photoreactions of cyclic imides. Examples of synthetic organic photochemistry

Phthalimide and Its Derivatives

Versuche zur Synthese pharmakologisch wirksamer Heterocyclen via Mannich-Reaktion, I. 3-Acetylpyridine und partiell hydrierte Chinoline†

Photoreaktionen des Phthalimids

References

Ueber einige substituirte Phtalimide und deren Ueberführung in die entsprechenden primären Amine

Related Papers (1)

Photocyclisierung von Phthalimid‐Mannichbasen