Cascade Assembly of Bridged N-Substituted Azaozonides: The Counterintuitive Role of Nitrogen Source Nucleophilicity

Cascade Assembly of Bridged N-Substituted Azaozonides: The Counterintuitive Role of Nitrogen Source Nucleophilicity Full article

Journal

Organic Letters
ISSN: 1523-7060 , E-ISSN: 1523-7052

Output data

Year: 2022, Volume: 24, Number: 36, Pages: 6582-6587 Pages count : 6 DOI: 10.1021/acs.orglett.2c02551

Authors

Yaremenko Ivan A. ¹ , Belyakova Yulia Yu. ¹ , Radulov Peter S. ¹ , Novikov Roman A. ¹ , Medvedev Michael G. ¹ , Krivoshchapov Nikolai V. ¹ , Alabugin Igor V. ² , Terent’ev Alexander O. ¹

Affiliations

1	N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prospect, Moscow 119991, Russian Federation
2	Department of Chemistry and Biochemistry, Florida State University, Tallahassee, Florida 32306, United States

Counterintuitively, the low basicity of the NH2 group in hydrazides makes them preferred nucleophiles for the synthesis of the N-substituted azaozonides in acid-catalyzed three-component condensation with 1,5-diketones and H2O2. In the case of more basic N sources, e.g., hydrazine and primary amines, such condensation does not occur under these reaction conditions. The method can be applied to a wide range of hydrazides and affords the target bicyclic azaozonides in 27–86% yields.

Yaremenko I.A. , Belyakova Y.Y. , Radulov P.S. , Novikov R.A. , Medvedev M.G. , Krivoshchapov N.V. , Alabugin I.V. , Terent’ev A.O.
Cascade Assembly of Bridged N-Substituted Azaozonides: The Counterintuitive Role of Nitrogen Source Nucleophilicity
Organic Letters. 2022. V.24. N36. P.6582-6587. DOI: 10.1021/acs.orglett.2c02551 WOS Scopus OpenAlex

Web of science:	WOS:000859683900001
Scopus:	2-s2.0-85137879710
OpenAlex:	W4294884837

DB	Citing
OpenAlex	10
Scopus	11
Web of science	9