ISSN:
0009-2940
Keywords:
Aminonicotinamide
;
Diazaphosphorinanones
;
Chemistry
;
Inorganic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Synthesis of Phosphorus-Containing Heterocycles from 2-Aminonicotinic AcidThe reaction of 2-aminonicotinic acid with ethyl chloroformate, followed by alkylation with NaH/Mel and decarboxylation with methylamine, led to N-methyl-2-(methylamino)nicotinamide (3). Treatment of 3 with PCl3 in the presence of triethylamine gave the phosphorinanone 4. Substitution of chlorine in 4 by the dimethylamino-, N,N,N′-trimethylethylenediamino-, or bis(2-chloroethyl)amino group furnished 5-7. Hydrolysis of 4 with small amounts of water formed the phosphoryl derivative 8 as the hydrochloride. The spirophosphoranes 9 and 10 were produced by reaction of 5 with hexafluoroacetone and tetrachloro-o-benzoquinone, respectively. In order to evaluate its coordination ability, the N,N,N′-trimethylethylenediamino-substituted diazaphosphorinanone 6 was allowed to react with the tetracarbonyl norbornadiene derivatives of chromium(0) and molybdenum(0). The cis-substituted tetracarbonyl complexes 12 and 13 were formed. In the reaction of 7 with dichloro(1,5-cyclooctadiene)platinum(II) the cis-disubstituted complex 15 was formed. A comparison of benzo- and pyrido-annulated phosphorinanones was made, and their differences were discussed. In the case of the compounds 2, 7, and 9 singlecrystal X-ray structure analyes were performed. In 9 the heterocycle C and N atoms are coplanar (the phosphorus lies 60 pm outside the plane); P and N(2) are displaced in 7 to the same side of the plane of the remaining four atoms.
Additional Material:
3 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/cber.19951280616
