Reductions of Other Heterocycles Containing One Nitrogen Atom

Reductions of Other Heterocycles Containing One Nitrogen Atom 

The reduction of phenanthridine to 5,6-dihydrophenanthridine (90, R = H) was readily accomplished by reaction with lithium aluminum hydride in ethereal solution.118 The same dihydrophenanthridine resulted from the lithium aluminum hydride reduction of 6-chloro-phenanthridine or phenanthridone,1180 thus confirming the position of saturation of the product.119 It is of interest to note that molecular complexes of phenanthridine and dihydrophenanthridine were not observed as products in this reduction as was the case in the metal hydride reduction of phenazine.119 

Phenanthridine methiodide underwent a facile reduction to N-methyl-5,6-dihydrophenanthridine (90, R = CHS) with lithium aluminum hydride in ethereal solution.120 It was found that the use of 

1176 Private communication from Professor A. I. Meyers, Louisiana State University, New Orleans, 1965. 

1178 J. O. Jilek, J. Pomykacfik, J. Metysova, J. Metys, and M. Protira, Collection Czech. Chem. Commun. 30, 463 (1965). 

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VI. Reductions of Other Heterocycles Containing One Nitrogen Atom... 

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