Cargando…
Two Annulated Azaheterocyclic Cores Readily Available from a Single Tetrahydroisoquinolonic Castagnoli–Cushman Precursor
A novel approach to indolo[3,2-c]isoquinoline and dibenzo[c,h][1,6]naphthyridine tetracyclic systems was discovered based on switchable reduction of 2-methoxy-3-(2-nitrophenyl)-1-oxo-1,2,3,4-tetrahydroisoquinoline-4-carboxylic acid prepared via Castagnoli–Cushman reaction. Reduction with ammonium fo...
Autores principales: | , , , |
---|---|
Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
MDPI
2020
|
Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7248902/ https://www.ncbi.nlm.nih.gov/pubmed/32354157 http://dx.doi.org/10.3390/molecules25092049 |
_version_ | 1783538478456242176 |
---|---|
author | Karchuganova, Elizaveta Bakulina, Olga Dar’in, Dmitry Krasavin, Mikhail |
author_facet | Karchuganova, Elizaveta Bakulina, Olga Dar’in, Dmitry Krasavin, Mikhail |
author_sort | Karchuganova, Elizaveta |
collection | PubMed |
description | A novel approach to indolo[3,2-c]isoquinoline and dibenzo[c,h][1,6]naphthyridine tetracyclic systems was discovered based on switchable reduction of 2-methoxy-3-(2-nitrophenyl)-1-oxo-1,2,3,4-tetrahydroisoquinoline-4-carboxylic acid prepared via Castagnoli–Cushman reaction. Reduction with ammonium formate resulted in the expected selective transformation of the nitro group (thus providing access to substituted dibenzo[c,h][1,6]naphthyridine via cyclization and dehydrogenation). However, attempted reduction with sodium sulfide initiated a previously unknown reaction cascade including double reduction, cyclization, and decarboxylation, leading to formation of indolo[3,2-c]isoquinoline polyheterocycle in one synthetic step. |
format | Online Article Text |
id | pubmed-7248902 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2020 |
publisher | MDPI |
record_format | MEDLINE/PubMed |
spelling | pubmed-72489022020-06-10 Two Annulated Azaheterocyclic Cores Readily Available from a Single Tetrahydroisoquinolonic Castagnoli–Cushman Precursor Karchuganova, Elizaveta Bakulina, Olga Dar’in, Dmitry Krasavin, Mikhail Molecules Communication A novel approach to indolo[3,2-c]isoquinoline and dibenzo[c,h][1,6]naphthyridine tetracyclic systems was discovered based on switchable reduction of 2-methoxy-3-(2-nitrophenyl)-1-oxo-1,2,3,4-tetrahydroisoquinoline-4-carboxylic acid prepared via Castagnoli–Cushman reaction. Reduction with ammonium formate resulted in the expected selective transformation of the nitro group (thus providing access to substituted dibenzo[c,h][1,6]naphthyridine via cyclization and dehydrogenation). However, attempted reduction with sodium sulfide initiated a previously unknown reaction cascade including double reduction, cyclization, and decarboxylation, leading to formation of indolo[3,2-c]isoquinoline polyheterocycle in one synthetic step. MDPI 2020-04-28 /pmc/articles/PMC7248902/ /pubmed/32354157 http://dx.doi.org/10.3390/molecules25092049 Text en © 2020 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/). |
spellingShingle | Communication Karchuganova, Elizaveta Bakulina, Olga Dar’in, Dmitry Krasavin, Mikhail Two Annulated Azaheterocyclic Cores Readily Available from a Single Tetrahydroisoquinolonic Castagnoli–Cushman Precursor |
title | Two Annulated Azaheterocyclic Cores Readily Available from a Single Tetrahydroisoquinolonic Castagnoli–Cushman Precursor |
title_full | Two Annulated Azaheterocyclic Cores Readily Available from a Single Tetrahydroisoquinolonic Castagnoli–Cushman Precursor |
title_fullStr | Two Annulated Azaheterocyclic Cores Readily Available from a Single Tetrahydroisoquinolonic Castagnoli–Cushman Precursor |
title_full_unstemmed | Two Annulated Azaheterocyclic Cores Readily Available from a Single Tetrahydroisoquinolonic Castagnoli–Cushman Precursor |
title_short | Two Annulated Azaheterocyclic Cores Readily Available from a Single Tetrahydroisoquinolonic Castagnoli–Cushman Precursor |
title_sort | two annulated azaheterocyclic cores readily available from a single tetrahydroisoquinolonic castagnoli–cushman precursor |
topic | Communication |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7248902/ https://www.ncbi.nlm.nih.gov/pubmed/32354157 http://dx.doi.org/10.3390/molecules25092049 |
work_keys_str_mv | AT karchuganovaelizaveta twoannulatedazaheterocycliccoresreadilyavailablefromasingletetrahydroisoquinoloniccastagnolicushmanprecursor AT bakulinaolga twoannulatedazaheterocycliccoresreadilyavailablefromasingletetrahydroisoquinoloniccastagnolicushmanprecursor AT darindmitry twoannulatedazaheterocycliccoresreadilyavailablefromasingletetrahydroisoquinoloniccastagnolicushmanprecursor AT krasavinmikhail twoannulatedazaheterocycliccoresreadilyavailablefromasingletetrahydroisoquinoloniccastagnolicushmanprecursor |