- Reactivity of Heterocyclic Compounds. VI. 2,6-Diaminopyrimidine-5-carbonitriles and 3,5-Dicyanopyridones from 2-Amino-4H-pyran-3,5-dicarbonitriles
-
The reaction of different 2-amino-4H-pyrans (1, 10) with guanidine affords 2,6-diaminopyrimidine derivatives (3).Treatment of the pyrans mentioned or their acetylated derivatives with trityl tetrafluoroborate does not yield pyrylium salts, and pyrid-2-one
- Seoane, C.,Soto, J. L.,Quinteiro, M.
-
-
- Synhesis of Heterocyclic Compounds. Part 46. The reactions of Malonamide and 2-Cyanoacetamide with Substituted Propenones
-
The synthesis of substituted 2-pyridone derivatives from malonamide (1) and 2-cyanoacetamide (2) is reported.Conjugate addition of these compounds to substituted propenones (3) and (4) leads to 6-hydroxy-2-piperidones, which can be dehydrated and aromatiz
- Soto, Jose L.,Seoane, Carlos,Zamorano, Pilar,Rubio, Maria J.,Monforte, Alejandro,Quinteiro, Margarita
-
p. 1681 - 1686
(2007/10/02)
-
- Synthesis of Heterocyclic Compounds, XXXVII Preparation of 4,6-Diaryl-1,2-dihydro-2-thioxo-3,5-pyridinedicarbonitriles and Related Compounds
-
The reaction of cyanothioacetamide (1) with α-benzoylcinnamonitriles 2 in basic ethanolic solution leads to 4,6-diaryl-1,2-dihydro-2-thioxo-3,5-pyridinedicarbonitriles 3 together with the disulfides 4.Treatment of 4 with 2-mercaptoethanol causes transformation into 3 which can lead to 4 upon reaction with either iodine-potassium iodide or dimethyl sulfoxide-trifluoroacetic acid.Methylation of 3 or 4 yields the expected methylthiopyridines 5.On the other hand, reaction of 3 with methyl chloroacetate allows the preparation of thienopyridines 8.
- Encinas, Maria Jesus Rubio,Seoane, Carlos,Soto, Jose L.
-
p. 213 - 222
(2007/10/02)
-
- SYNTHESIS OF HETEROCYCLIC COMPOUNDS XXXV THIOPYRIDONES FROM α-BENZOYLCINNAMONITRILES
-
2-Pyridothiones (IV) are obtained from the reaction of α-bonzoylcinnamonitriles (I) with cyanothioacetamide (II).Disulphides V result as well from the reaction.Transformation of IV into V and of V into IV, as well as methylation of IV and their hydrolytic conversion into pyridones VI are also described.Pyridones VI can also be obtained from methylthiopyridines VIII.
- a. Jesus,Seoane, Carlos,Soto, Jose L.
-
p. 783 - 786
(2007/10/02)
-
- Ring Transformations of 4H-Pyrans. Pyridines from 2-Amino-4H-Pyrans
-
Ring transformations of 4H-pyrans into pyridines are reported.Treatment of 2-amino-4,6-diaryl-3,5-dicyano-4H-pyrans (I) with nitrosylsulfuric acid brings about their transformation into 3,5-dicyano-4,6-diaryl-2-pyridones (VI) which can also be obtained fr
- Seoane, Carlos,Soto, Jose L.,Zamorano, Pilar,Quinteiro, Margarita
-
p. 309 - 314
(2007/10/02)
-
- SYNTHESIS OF HETEROCYCLIC COMPOUNDS XIX PREPARATION OF 4,6-DIARYL-3,5-DICYANO-2-PYRIDONES
-
Reaction of cyanoacetamide with α-benzoylcinnamonitriles (I) leads to a new series of 4,6-diaryl-3,5-dicyano-2-pyridones (IV). The initial Michael's addition is followed by a cyclization to a 6-hydroxy-2-piperidone ring (II), whose acid dehydration gives rise to 3,4-dihydro-2-pyridones (III).The latter are easily aromatized to 4,6-diaryl-3,5-dicyano-2-pyridones (IV) by treatment with sodium nitrite in sulfuric acid.
- Seoane, C.,Soto, J. L.,Zamorano, M. P.
-
p. 639 - 642
(2007/10/02)
-