Design and syntheses of C-4 4-(1-methoxycarbonyl-1,2-dihydropyridyl)-, and 3-[1-methoxycarbonyl-1,2-(and 1,6-)dihydropyridyl]-, derivatives of alkyl 1,4-dihydro-2,6-dimethyl-3-nitro-5-pyridinecarboxylates with cardiospecific calcium channel agonist activity
β Scribed by Manian Ramesh; Wandikayi C. Matowe; Michael W. Wolowyk; Edward E. Knaus
- Publisher
- John Wiley and Sons
- Year
- 2000
- Tongue
- English
- Weight
- 148 KB
- Volume
- 49
- Category
- Article
- ISSN
- 0272-4391
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The novel and versatile cyanomethyl 2amino-4-methylthiazolyl ketone (5) was prepared by treatment of bromomethyl 2-amino-4-methyl thiazolyl ketone (4) with potassium cyanide. Reaction of 5 with heterocyclic diazonium salts 6a,b and 10 afforded the corresponding hydrazones 7a,b and 11, respectively.
The total assignment of the 1 H and 13 C NMR spectra of 24 cis-endo and 15 cis-exo diastereoisomers of C-1-substituted 2,4-dimethyl-8-oxabicyclo[3.2.1]oct-6-en-3-one derivatives was deduced from the concerted application of DEPT, COSY, HETCOR, HMBC, HMQC and PS-NOESY experiments. The relative stereo