Synthesis and Facile Dearomatization of Highly Electrophilic Nitroisoxazolo[4,3-<i>b</i>]pyridines
A number of novel 6-R-isoxazolo[4,3-<i>b</i>]pyridines were synthesized and their reactions with neutral C-nucleophiles (1,3-dicarbonyl compounds, π-excessive (het)arenes, dienes) were studied. The reaction rate was found to be dependent on the nature of the substituent 6-R. The most rea...
Main Authors: | , , , , |
---|---|
Format: | Article |
Language: | English |
Published: |
MDPI AG
2020-05-01
|
Series: | Molecules |
Subjects: | |
Online Access: | https://www.mdpi.com/1420-3049/25/9/2194 |
id |
doaj-fbe63aca3edf4683ab7cf774ce877519 |
---|---|
record_format |
Article |
spelling |
doaj-fbe63aca3edf4683ab7cf774ce8775192020-11-25T03:10:02ZengMDPI AGMolecules1420-30492020-05-01252194219410.3390/molecules25092194Synthesis and Facile Dearomatization of Highly Electrophilic Nitroisoxazolo[4,3-<i>b</i>]pyridinesMaxim A. Bastrakov0Alexey K. Fedorenko1Alexey M. Starosotnikov2Ivan V. Fedyanin3Vladimir A. Kokorekin4N.D. Zelinsky Institute of Organic Chemistry RAS; Leninsky prosp. 47, 119991 Moscow, RussiaN.D. Zelinsky Institute of Organic Chemistry RAS; Leninsky prosp. 47, 119991 Moscow, RussiaN.D. Zelinsky Institute of Organic Chemistry RAS; Leninsky prosp. 47, 119991 Moscow, RussiaA.N. Nesmeyanov Institute of Organoelement Compounds, Vavilova str. 28, 119991 Moscow, RussiaN.D. Zelinsky Institute of Organic Chemistry RAS; Leninsky prosp. 47, 119991 Moscow, RussiaA number of novel 6-R-isoxazolo[4,3-<i>b</i>]pyridines were synthesized and their reactions with neutral C-nucleophiles (1,3-dicarbonyl compounds, π-excessive (het)arenes, dienes) were studied. The reaction rate was found to be dependent on the nature of the substituent 6-R. The most reactive 6-nitroisoxazolo[4,3-<i>b</i>]pyridines are able to add C-nucleophiles in the absence of a base under mild conditions. In addition, these compounds readily undergo [4+2]-cycloaddition reactions on aromatic bonds C=C(NO<sub>2</sub>) of the pyridine ring, thus indicating the superelectrophilic nature of 6-NO<sub>2</sub>-isoxazolo[4,3-<i>b</i>]pyridines.https://www.mdpi.com/1420-3049/25/9/2194nitro groupnitropyridinesisoxazolo[4,3-<i>b</i>]pyridines1,4-dihydropyridinesnucleophilic additionDiels-Alder reaction |
collection |
DOAJ |
language |
English |
format |
Article |
sources |
DOAJ |
author |
Maxim A. Bastrakov Alexey K. Fedorenko Alexey M. Starosotnikov Ivan V. Fedyanin Vladimir A. Kokorekin |
spellingShingle |
Maxim A. Bastrakov Alexey K. Fedorenko Alexey M. Starosotnikov Ivan V. Fedyanin Vladimir A. Kokorekin Synthesis and Facile Dearomatization of Highly Electrophilic Nitroisoxazolo[4,3-<i>b</i>]pyridines Molecules nitro group nitropyridines isoxazolo[4,3-<i>b</i>]pyridines 1,4-dihydropyridines nucleophilic addition Diels-Alder reaction |
author_facet |
Maxim A. Bastrakov Alexey K. Fedorenko Alexey M. Starosotnikov Ivan V. Fedyanin Vladimir A. Kokorekin |
author_sort |
Maxim A. Bastrakov |
title |
Synthesis and Facile Dearomatization of Highly Electrophilic Nitroisoxazolo[4,3-<i>b</i>]pyridines |
title_short |
Synthesis and Facile Dearomatization of Highly Electrophilic Nitroisoxazolo[4,3-<i>b</i>]pyridines |
title_full |
Synthesis and Facile Dearomatization of Highly Electrophilic Nitroisoxazolo[4,3-<i>b</i>]pyridines |
title_fullStr |
Synthesis and Facile Dearomatization of Highly Electrophilic Nitroisoxazolo[4,3-<i>b</i>]pyridines |
title_full_unstemmed |
Synthesis and Facile Dearomatization of Highly Electrophilic Nitroisoxazolo[4,3-<i>b</i>]pyridines |
title_sort |
synthesis and facile dearomatization of highly electrophilic nitroisoxazolo[4,3-<i>b</i>]pyridines |
publisher |
MDPI AG |
series |
Molecules |
issn |
1420-3049 |
publishDate |
2020-05-01 |
description |
A number of novel 6-R-isoxazolo[4,3-<i>b</i>]pyridines were synthesized and their reactions with neutral C-nucleophiles (1,3-dicarbonyl compounds, π-excessive (het)arenes, dienes) were studied. The reaction rate was found to be dependent on the nature of the substituent 6-R. The most reactive 6-nitroisoxazolo[4,3-<i>b</i>]pyridines are able to add C-nucleophiles in the absence of a base under mild conditions. In addition, these compounds readily undergo [4+2]-cycloaddition reactions on aromatic bonds C=C(NO<sub>2</sub>) of the pyridine ring, thus indicating the superelectrophilic nature of 6-NO<sub>2</sub>-isoxazolo[4,3-<i>b</i>]pyridines. |
topic |
nitro group nitropyridines isoxazolo[4,3-<i>b</i>]pyridines 1,4-dihydropyridines nucleophilic addition Diels-Alder reaction |
url |
https://www.mdpi.com/1420-3049/25/9/2194 |
work_keys_str_mv |
AT maximabastrakov synthesisandfaciledearomatizationofhighlyelectrophilicnitroisoxazolo43ibipyridines AT alexeykfedorenko synthesisandfaciledearomatizationofhighlyelectrophilicnitroisoxazolo43ibipyridines AT alexeymstarosotnikov synthesisandfaciledearomatizationofhighlyelectrophilicnitroisoxazolo43ibipyridines AT ivanvfedyanin synthesisandfaciledearomatizationofhighlyelectrophilicnitroisoxazolo43ibipyridines AT vladimirakokorekin synthesisandfaciledearomatizationofhighlyelectrophilicnitroisoxazolo43ibipyridines |
_version_ |
1724661000738701312 |