Synthesis of 2,3-Dihydrobenzo[B][1,4]Dioxins by the Hetero-Diels-Alder Reaction Based on 3,5-Di(tert-butyl)-6-nitro-1,2-benzoquinone

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Abstract

A sterically hindered o-quinone activated by a nitro group can act as an effective diene in the Diels-Alder reaction. The interaction of a twofold excess of 3,5-di-(tert-butyl)-6-nitro-1,2-benzoquinone in the reaction with arylamines in an isopropanol/methylethyl ketone medium (1 : 1) leads to the formation of derivatives ((2,3-dihydrobenzo[ b][1,4]dioxin-2-yl)oxy)-3-nitrophenols.

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About the authors

E. P. Ivakhnenko

Southern Federal University

Author for correspondence.
Email: ivakhnenko@sfedu.ru
ORCID iD: 0000-0003-0338-6466
Russian Federation, Rostov-on-Don

V. I. Malay

North Caucasus Federal University

Email: malay@sfedu.ru
ORCID iD: 0000-0002-5302-743X
Russian Federation, Stavropol

O. P. Demidov

North Caucasus Federal University

Email: ivakhnenko@sfedu.ru
ORCID iD: 0000-0002-3586-0487
Russian Federation, Stavropol

N. I. Merezhko

Southern Federal University

Email: ivakhnenko@sfedu.ru
ORCID iD: 0009-0000-2672-4072
Russian Federation, Rostov-on-Don

S. E. Kislitsin

Southern Federal University

Email: ivakhnenko@sfedu.ru
ORCID iD: 0009-0007-0873-696X
Russian Federation, Rostov-on-Don

V. I. Minkin

Southern Federal University

Email: ivakhnenko@sfedu.ru
ORCID iD: 0000-0001-6096-503X
Russian Federation, Rostov-on-Don

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Supplementary files

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2. Scheme 1. Synthesis of 6-(tert-butyl)-2-methyl-1-aryl-1H-cyclopenta[b]pyridine-4,5-diones 2

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3. Scheme 2. Synthesis of dihydrobenzo[b][1,4]dioxin-2-yl-oxy-3-nitrophenols 4

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4. Fig. 1. Molecular structure of compounds 4 (c)

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5. Fig. 2. Side view in two projections of dioxin fragment 4 (c). Hydrogen atoms are omitted for clarity

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