Carboxamides 3 ,5 -dichloro-

Certain pyridines react with Grignard reagents in the 1,4-manner when substituted by electron-withdrawing groups such as a carboxamide <2000J(P1)4245, 2005JOC2000>. The intermediate dihydropyridine can conveniently be oxidized to the pyridine structure. An example of this is seen in the reaction of 6-chloronicotinic acid derivative 125 with an excess of o-tolylmagnesium chloride, followed by oxidation with 2,3-dichloro-5,6-dicyano-l,4-benzoquinone... 

Dichloro-/V,/V-diethyl-1,8-naphthyridine-3-carboxamide (35) with N,N diethylisobutyrohydrazide gave 5-chloro-fV,fV-diethyl-9-isopropyl[ 1,2,4]tria-zolo 4,3- 1,8 Inaphthyridine-1 -carboxamide (36) (Dowtherm A, 155°C ... 

Oxidation of Schiff bases of the monoamide 8 derived from diamino-maleonitrile gives 4-cyanoimidazole-5-carboxamides (Eq. 4). A new synthesis of 2-formyl-4-methyl-l-phenylimidazole 3-oxide (10) involves the fluoride-ion-promoted cyclization of the trimethylsilyl ether of JV-dichloro-acetyl-A-phenylaminopropanone oxime (9). ... 

Hurst DP, Lynch DL, Barnett-Norris J, Hyatt SM, Seltzman HH, Zhong M, Song Z-H, Nie J, Lewis D, Reggio PH (2002) N-(Piperidin-l-yl)-5-(4-chlorophenyl)-l-(2,4-dichloro-phenyl)-4-metliyl-lH-pyrazole-3-carboxamide (SR141716A) interaction with LYS 3.28(192) is crucial for its inverse agonism at the cannabinoid CBI receptor. Mol Pharmacol 62 1274-1287... 

Substituted 4,6-diaminopyrimidine-5-carbaldehydes, available by ammonolysis of the corresponding dichloro compounds, have been condensed with A-substituted cyanoacetamides in the presence of ethanolic sodium ethoxide at reflux temperature to give 4,7-diaminopyri-do[2,3-f/]pyrimidine-6-carboxamides 25.182... 

NBS is relatively stable, but it should be noted that A-halogenated carboxamides and carboximides such as l,3-dichloro-5,5-dimethylhydantoin, A-chlorosuccinimide, and also NBS are thermally labile and may decompose explosively.353... 

Literature reports over the past hundred years and their chemistry have been reviewed in 1964 [5] and in 1967 [6] and proved their importance in medicinal and technical applications. Structurally, simple 5-amino-l-tertbutylp3rrazole-4-carboxamide I was found to inhibit p56 Lck [7]. The simple N-phenyl amide of 5-amino-l,3-dimethylpyrazole-4-carboxylic add II has been shown to exhibit antifungal activity [8]. The 5-amino-l-(2,6-dichloro-4-trifluoromethyl) phenyl)-4-(3-ethoxyphenyl)-3-methyl thiopyrazole has been described as a potent GABA (y-aminobutyric acid) inhibitor with selectivity toward insect versus mammalian receptors [9]. 5-Amino-4-benzoyl-3-methylthio-l-(2,4,6-trichlorophenyl)pyrazole III has been reported as a potent corti-cotrophin-releasing factor-1 (CRF-1) receptor antagonist [10]. The 5-amino-l-(4-methylphenyl) pyrazole IV has been tested as an NPY5 antagonist [11]. 

CA Index Name Spiro[isobenzofuran-l(3//),9 -[9//] xanthene]-5-carboxamide, N-[4-[bis(2-pjnidinylmethyl) amino]phenyl]-2, 7 -dichloro-3, 6 -dihydroxy-3-oxo-, potassium salt (1 2)... 

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