4-Amino-2-butyl-7-methoxycarbonylthiazolo[4,5-<i>c</i>]quinoline
4-Amino-imidazo-, oxazolo-, and thiazoloquinolines are key structural scaffolds in the design of nucleoside base analogs for use as therapeutic agents. Current strategies for arriving at diverse substitutions at the C6–C9 positions of the thiazolo- and oxazoloquinolines, however, are limited due to...
| Main Authors: | , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
MDPI AG
2021-12-01
|
| Series: | Molbank |
| Subjects: | |
| Online Access: | https://www.mdpi.com/1422-8599/2021/4/M1305 |
| _version_ | 1797502175149031424 |
|---|---|
| author | Peter G. Larson David M. Ferguson |
| author_facet | Peter G. Larson David M. Ferguson |
| author_sort | Peter G. Larson |
| collection | DOAJ |
| description | 4-Amino-imidazo-, oxazolo-, and thiazoloquinolines are key structural scaffolds in the design of nucleoside base analogs for use as therapeutic agents. Current strategies for arriving at diverse substitutions at the C6–C9 positions of the thiazolo- and oxazoloquinolines, however, are limited due to difficulties in arriving at the thiazoloquinoline-5N-oxide intermediate using electron deficient aromatic systems. Here, we demonstrate a synthetic route to obtain substituted thiazoloquinolines with electron-withdrawing groups at the C7 position. The target compound, 4-amino-2-butyl-7-methoxycarbonylthiazolo[4,5-<i>c</i>]quinoline, is obtained in eight steps using a 7-bromo surrogate as a precursor to the successful generation of the N-oxide intermediate, and final transformation via Pd-mediated C7-acylation. |
| first_indexed | 2024-03-10T03:30:09Z |
| format | Article |
| id | doaj.art-4fc1aecdefa848d9a1348d095b6fe499 |
| institution | Directory Open Access Journal |
| issn | 1422-8599 |
| language | English |
| last_indexed | 2024-03-10T03:30:09Z |
| publishDate | 2021-12-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molbank |
| spelling | doaj.art-4fc1aecdefa848d9a1348d095b6fe4992023-11-23T09:43:39ZengMDPI AGMolbank1422-85992021-12-0120214M130510.3390/M13054-Amino-2-butyl-7-methoxycarbonylthiazolo[4,5-<i>c</i>]quinolinePeter G. Larson0David M. Ferguson1Department of Medicinal Chemistry, University of Minnesota, Minneapolis, MN 55455, USADepartment of Medicinal Chemistry, University of Minnesota, Minneapolis, MN 55455, USA4-Amino-imidazo-, oxazolo-, and thiazoloquinolines are key structural scaffolds in the design of nucleoside base analogs for use as therapeutic agents. Current strategies for arriving at diverse substitutions at the C6–C9 positions of the thiazolo- and oxazoloquinolines, however, are limited due to difficulties in arriving at the thiazoloquinoline-5N-oxide intermediate using electron deficient aromatic systems. Here, we demonstrate a synthetic route to obtain substituted thiazoloquinolines with electron-withdrawing groups at the C7 position. The target compound, 4-amino-2-butyl-7-methoxycarbonylthiazolo[4,5-<i>c</i>]quinoline, is obtained in eight steps using a 7-bromo surrogate as a precursor to the successful generation of the N-oxide intermediate, and final transformation via Pd-mediated C7-acylation.https://www.mdpi.com/1422-8599/2021/4/M1305nitrogen heterocyclesthiazoloquinoline1,3-dipolar cycloadditionPd-catalyzed carbonylationquinoline-N-oxide |
| spellingShingle | Peter G. Larson David M. Ferguson 4-Amino-2-butyl-7-methoxycarbonylthiazolo[4,5-<i>c</i>]quinoline Molbank nitrogen heterocycles thiazoloquinoline 1,3-dipolar cycloaddition Pd-catalyzed carbonylation quinoline-N-oxide |
| title | 4-Amino-2-butyl-7-methoxycarbonylthiazolo[4,5-<i>c</i>]quinoline |
| title_full | 4-Amino-2-butyl-7-methoxycarbonylthiazolo[4,5-<i>c</i>]quinoline |
| title_fullStr | 4-Amino-2-butyl-7-methoxycarbonylthiazolo[4,5-<i>c</i>]quinoline |
| title_full_unstemmed | 4-Amino-2-butyl-7-methoxycarbonylthiazolo[4,5-<i>c</i>]quinoline |
| title_short | 4-Amino-2-butyl-7-methoxycarbonylthiazolo[4,5-<i>c</i>]quinoline |
| title_sort | 4 amino 2 butyl 7 methoxycarbonylthiazolo 4 5 i c i quinoline |
| topic | nitrogen heterocycles thiazoloquinoline 1,3-dipolar cycloaddition Pd-catalyzed carbonylation quinoline-N-oxide |
| url | https://www.mdpi.com/1422-8599/2021/4/M1305 |
| work_keys_str_mv | AT peterglarson 4amino2butyl7methoxycarbonylthiazolo45iciquinoline AT davidmferguson 4amino2butyl7methoxycarbonylthiazolo45iciquinoline |