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...

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Main Authors:	Maxim A. Bastrakov, Alexey K. Fedorenko, Alexey M. Starosotnikov, Ivan V. Fedyanin, Vladimir A. Kokorekin
Format:	Article
Language:	English
Published:	MDPI AG 2020-05-01
Series:	Molecules
Subjects:	nitro group nitropyridines isoxazolo[4,3-<i>b</i>]pyridines 1,4-dihydropyridines nucleophilic addition Diels-Alder reaction
Online Access:	https://www.mdpi.com/1420-3049/25/9/2194

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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
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Synthesis and Facile Dearomatization of Highly Electrophilic Nitroisoxazolo[4,3-<i>b</i>]pyridines

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