Methyl Isonicotinate Research Articles

Studies on the syntheses of heterocyclic compounds. Part CCCLXXXIX. An alternative synthesis of de-ethyldasycarpidone

The synthesis of (±)-de-ethyldasycarpidone (V) is described. The key step involves condensation of indolylmagnesium bromide with methyl isonicotinate 1-oxide to afford the pyridylindole (VI). Hydrogenation of the methiodide of the latter over platinum yielded a mixture of stereoisomers of the amino-esters (X). Normal saponification of the compound (Xa) afforded the amino-acid (XI) which was heated with polyphosphoric acid to give de-ethyldasycarpidone (V).

Keteneおよびその誘導体の研究 (第7報)

Isoquinoline, lepidine, and methyl isonicotinate react with diketene to form Wollenberg-type compounds (III, IV, and V). These compounds form dehydro derivatives by dehydrogenation. Hydrolysis of the dehydro compound of III affords compounds with the γ-pyrone ring opened. The ultraviolet absorption spectra of these compounds endorsed these reactions. Examination of their infrared absorption spectra indicated that the Wollenberg-type compounds previously reported, including pyridine-diketene adduct (I) and quinoline-diketene adduct (II), take the a-type structure.

Betaine Formation during Hydrogenation of Methyl Isonicotinate1a

Betaine Formation during Hydrogenation of Methyl Isonicotinate^1a

Antistimulant actions of gamma-aminobutyric acid and its derivatives on the guinea-pig ileum.

The anti-stimulant (Ach, 5-HT, nicotine, histamine) actions of GABA and its derivatives on the guinea-pig ileum were investigated.1. The anti-Ach action of GABA was weak and variable. The stimulant effect of 5×10-10-10-9 mole/l Ach was reduced by 42% on the average of 11 experiments.2. The anti-Ach action of N-methyl-GABA was about a tenth of that of GABA. N-Dimethyl-GABA produced hardly it an N-trimethyl-GABA had a synergestic action with Ach.3. N-Acetyl-GABA had a slightly weaker anti-Ach action than N-methyl-GABA and N-phenyl-GABA had a far weaker one.4. GABA-methylester and N-methyl-GABA-methyiester had not any anti-Ach action. N-methyl-GABA-butylester and N-methyl-GABA benzylester had a much stronger anti-Ach action than GABA. N-phenyl-GABA-methylester had a slightly stronger one.5. In the anti-5-HT action of GABA, N-substitution by methyl-, phenyl-and acetyl-group decreased the activity more severely than in the anti-Ach action.6. N-Methyl-GABA-butylester and N-methyl-GABA-benzylester were similar to GABA as the antagonist of 5-HT. N-Phenyl-GABA-methylester was somewhat inferior to GABA.7. The anti-nicotine action of GABA was also decreased by N-substitution with methyl-, phenyl-and acetyl-group. But, the reduction of potency by these structural changes was far less than in the anti-Ach action.8. N-Methyl-GABA-butylester and N-methyl-GABA-benzylester had a very stronger anti-nicotine action than GABA, while N-phenyl-GABA-methylester had a slightly higher potency.9. In all the actions above mentioned, N-methyl-GABA-butylester was somewhat superior to N-methyl-GABA-benzylester.10. In all the actions, the activity of GABOB was a half or a third of that of GABA.11. Methylesters of nicotinic acid and isonicotinic acid had a stronger anti-Ach action or anti-5-HT action than the acids and their activity was about a tenth of that of GABA. Methyl nicotinate and methyl isonicotinate were superior to their acids in anti-nicotine action, too, and their activities was more powerful than GABA.12. GABA had not any anti-histamine action, but N-methyl-GABA-butylester and N-methyl-GABA-benzylester had a considerably strong action.