- Synthesis of Phosphorus-Containing Heterocycles from 2-Aminonicotinic Acid
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The reaction of 2-aminonicotinic acid with ethyl chloroformate, followed by alkylation with NaH/MeI 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 comparision of benzo- and pyrido-annulated phosphorinanones was made, and their differences were discussed.In the case of the compounds 2, 7, and 9 single-crystal X-ray structure analyses 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. - Key Words: Aminonicotinamide/ Diazaphosphorinanones
- Sonnenburg, Ralf,Neda, Ion,Fischer, Axel,Jones, Peter G.,Schmutzler, Reinhard
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p. 627 - 634
(2007/10/02)
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- REACTIONS OF αω-BIS(BROMOMAGNESIO)ALKANES WITH HETEROCYCLIC ANHYDRIDES. A NOVEL SYNTHESIS OF FIVE AND SIX-MEMBERED 1-(o-AMINOPHENYL)CYCLOALKANOLS AND 1-(2'-AMINO-3'-PYRIDINYL)CYCLOALKANOLS
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Isatoic anhydrides and azaisatoic anhydrides are converted by reaction with 1,4-bis(bromomagnesio)butane and 1,5-bis(bromomagnesio)pentane into the corresponding 1-(o-aminophenyl)cycloalkanols and 1-(2'-amino-3'pyridinyl)cycloalcanols.
- Canonne, P.,Boulanger, R.,Chantegrel, B.
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p. 663 - 668
(2007/10/02)
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- The Chemistry of 3-Azaisatoic Anhydrides. Synthesis and Reactions of Polyaza Heterocycles
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The preparation of a variety of N-substituted 3-azaisotoic anhydrides 3 and 8 is described.These anhydrides reacted with thiopseudoureas to give interesting bicyclic, tricyclic, and tetracyclic heterocycles many of which are new ring systems.One such hete
- Coppola, Gary M.,Fraser, James D.,Hardtmann, Goetz E.,Shapiro, Michael J.
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p. 193 - 206
(2007/10/02)
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- 4-Amino-3-carboxy or cyano-1,2-dihydro-2-oxo-1,8-naphthyridine derivatives
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4-Amino-3-carboxy or cyano-1,2-dihydro-2-oxo-1,8-naphthyridine derivatives are anti-secretory agents for use in the treatment of peptic ulcer disease.
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- 1-Alkyl-4-amino-3-(3-aminotriazolo)-1,8 naphthyridine-2-ones
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1-alkyl-4-amino-3-(3-aminotriazolo)-1,8-naphthyridine-2-ones are antihypertensive agents.
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- N-substituted-3-azaisatoic anhydrides
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The novel 3,4-dihydro-1,3 dioxo-1,4 pyrido-(2,3-d)(1,3) oxazine compounds of this invention are useful as intermediates in the preparation of pharmaceutically active pyridopyrimidine-one compounds.
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