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The synthesis of thiaolivacine and related compounds
Author(s) -
Campaigne E.,
Ashby John
Publication year - 1969
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570060617
Subject(s) - isoquinoline , chemistry , aldehyde , acetal , ring (chemistry) , derivative (finance) , schiff base , medicinal chemistry , stereochemistry , organic chemistry , catalysis , financial economics , economics
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.