The synthesis of thiaolivacine and related compounds
- 1 December 1969
- journal article
- research article
- Published by Wiley in Journal of Heterocyclic Chemistry
- Vol. 6 (6) , 875-878
- https://doi.org/10.1002/jhet.5570060617
Abstract
1,5‐Dimethylbenzothieno[2,3‐g]isoquinoline (thiaolivacine) has been prepared from the nitro‐vinyl derivative of 4‐methyl‐3‐dibenzothiophenecarboxaldehyde. Using the same aldehyde, 4‐des‐methylisothiaolivacine was prepared by formation of the Schiff's base with aminoacetaldehyde diethyl acetal followed by cyclization. Similar methods yielded the pyrido‐N‐isomer, 1‐des‐methylthiaolivacine, from 4‐methyl‐2‐dibenzothiophenecarboxaldehyde. The thiaolivacine parent unsubstituted ring system, benzothieno[2,3‐g]isoquinoline, was prepared from 2‐dibenzothio‐pheneearboxaldehyde by the aminoacetaldehyde approach, as was the corresponding oxygen analog, benzofuro[2,3‐g]isoquinoline, from 2‐dibenzofurancarboxaldehyde. The 100 MHz spectra of these fused isoquinolines are recorded and correlated.Keywords
This publication has 6 references indexed in Scilit:
- Some methyl substituted benzo[b]naphtho[2,3‐d]thiophenesJournal of Heterocyclic Chemistry, 1969
- The NMR spectra of some substituted dibenzothiophenesJournal of Heterocyclic Chemistry, 1969
- Substitution reactions of 4‐methyldibenzothiopheneJournal of Heterocyclic Chemistry, 1969
- Ellipticine analogs: Oxygen and sulfur isosteresJournal of Heterocyclic Chemistry, 1969
- Synthesis of thia‐ellipticine, 5,11‐dimethylbenzothieno[2,3‐g]isoquinolineJournal of Heterocyclic Chemistry, 1968
- Dibenzofuran. VIII. Heteronuclear SubstitutionJournal of the American Chemical Society, 1939