Divergent Synthesis of Five-Membered Nitrogen Heterocycles via Cascade Reactions of 4-Arylfuroxans

Daniil A. Chaplygin; Ivan V. Ananyev; Leonid L. Fershtat; Nina N. Makhova

doi:10.1055/s-0040-1707393

Synthesis, Inhaltsverzeichnis

Synthesis 2020; 52(18): 2667-2678
DOI: 10.1055/s-0040-1707393

paper

Divergent Synthesis of Five-Membered Nitrogen Heterocycles via Cascade Reactions of 4-Arylfuroxans

Daniil A. Chaplygin

^aN. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 119991 Leninsky prosp., 47, Moscow, Russian Federation eMail: fershtat@bk.ru

,

Ivan V. Ananyev

^bA. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 119991, Vavilova str., 28, Moscow, Russian Federation

^cNational Research University Higher School of Economics, 101000, Moscow, Russian Federation

,

Leonid L. Fershtat ∗

^aN. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 119991 Leninsky prosp., 47, Moscow, Russian Federation eMail: fershtat@bk.ru

,

Nina N. Makhova

^aN. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 119991 Leninsky prosp., 47, Moscow, Russian Federation eMail: fershtat@bk.ru

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Abstract

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Abstract

A novel method for the synthesis of a diverse series of functionally substituted five-membered heterocyclic compounds via atom-economic, regio-, and diastereoselective one-pot reaction cascade was developed. This approach involves a ring opening in 4-arylfuroxans to α-oximinoarylacetonitrile oxides followed by [3+2] cycloaddition to various dipolarophiles to afford multisubstituted isoxazoles and isoxazolines. Subsequent azole–azole rearrangement of (oximino)isoxazolines/-isoxazoles, which can be conducted in a one-pot manner, results into functionally substituted furazans formation. The developed protocol is operationally simple, proceeds in mild conditions and with high yields of target heterocyclic systems. Overall, this study represents a new mode of isoxazole and 1,2,5-oxadiazole functionalization strategy, which is useful in medicinal and materials chemistry.

Key words

nitrogen heterocycles - 1,2,5-oxadiazole - rearrangement - cascade reactions - [3+2] cycloaddition

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