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

Synthesis and Facile Dearomatization of Highly Electrophilic Nitroisoxazolo[4,3-b]pyridines Full article

Journal

Molecules
ISSN: 1420-3049

Output data

Year: 2020, Volume: 25, Number: 9, Article number : 2194, Pages count : DOI: 10.3390/molecules25092194

Authors

Bastrakov Maxim A. ¹ , Fedorenko Alexey K. ^2,1 , Starosotnikov Alexey M. ¹ , Fedyanin Ivan V. ³ , Kokorekin Vladimir A. ¹

Affiliations

1	N.D. Zelinsky Institute of Organic Chemistry RAS; Leninsky prosp. 47, 119991 Moscow, Russia.
2	Chemistry Department, Lomonosov Moscow State University, Leninskie gory, 1/3, 119991 Moscow, Russia
3	A.N. Nesmeyanov Institute of Organoelement Compounds, Vavilova str. 28, 119991 Moscow, Russia

A number of novel 6-R-isoxazolo[4,3-b]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-b]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(NO2) of the pyridine ring, thus indicating the superelectrophilic nature of 6-NO2-isoxazolo[4,3-b]pyridines.

Bastrakov M.A. , Fedorenko A.K. , Starosotnikov A.M. , Fedyanin I.V. , Kokorekin V.A.
Synthesis and Facile Dearomatization of Highly Electrophilic Nitroisoxazolo[4,3-b]pyridines
Molecules. 2020. V.25. N9. 2194 . DOI: 10.3390/molecules25092194 WOS Scopus OpenAlex

Web of science:	WOS:000535695900190
Scopus:	2-s2.0-85084546259
OpenAlex:	W3021858945

DB	Citing
OpenAlex	12
Scopus	11
Web of science	9