Concepedia

The chemistry of cyclic enaminoketones. III. Synthesis of bi‐ and tricyclic enaminoketones from enamine esters and nitriles

A. I. MEYERS, Alden H. Reine, Jagadish C. Sircar, K. Babu Rao, S. SINGH, Hans Weidmann, Martin O. Fitzpatrick

Journal of Heterocyclic Chemistry · 1968 · 14 citations · 10 references

DOI

Concepts

Abstract

Abstract The cyclization of enamines derived from β‐aminoesters and β‐aminonitriles into bi‐ and tricyclic enaminoketones ( 6,9,13 and 24 ) has been investigated. The enamines derived from aminonitriles cyclize smoothly with magnesium perchlorate in benzene or toluene, whereas the enamines derived from aminoesters cyclize spontaneously during their formation. The scope and limitation of this process is discussed.

References

10

Basically Substituted Aliphatic Nitriles and their Catalytic Reduction to Amines<sup>1</sup>

Frank C. Whitmore, Harry S. Mosher, Robert R. Adams et al. · Journal of the American Chemical Society · 1944 · 88 citations

, , +9

Effect of Structure on Reactivity.<sup>1</sup> I. Ammonolysis of Esters with Special Reference to the Electron Release Effects of Alkyl and Aryl Groups

Maxwell Gordon, John G. Miller, Allan R. Day · Journal of the American Chemical Society · 1948 · 60 citations

, , +9

Azasteroids. V. The Direct Conversion of 1-(Carboethoxymethyl)-1,2,3,4-tetrahydroisoquinolines and Cyclic Ketones into Benzo[a]cycloalkano[f]quinolizinones. An Example of Enamine Acylation by an Ester Function<sup>1,2</sup>

W. Sobótka, W. N. Beverung, Gabriel Muñoz et al. · The Journal of Organic Chemistry · 1965 · 33 citations

, , +12

Synthesis of Substituted Pyrrolidines and Pyrrolizidines

Roger Adams, S. MIYANO, M. D. NAIR · Journal of the American Chemical Society · 1961 · 29 citations

, , +8

Decahydrochinolole, 1. Teil. Synthese und Konfiguration der epimeren 1‐Methyl‐4‐hydroxy‐<i>trans</i>‐decahydrochinoline

C. A. Grob, H. J. Lutz · Helvetica Chimica Acta · 1965 · 15 citations

, , +6