Reaction of quinaldine with 4,6-di (tert-butyl)-3-nitro-1,2-benzoquinone. Dependence of the outcome on the reaction conditions and a deeper insight into the mechanism

被引：0

作者：

Krasnikova, Tatyana A. ^{[1
]}

Sayapin, Yurii A. ^{[2
]}

Tupaeva, Inna O. ^{[1
]}

Gusakov, Eugeny A. ^{[1
]}

Ozhogin, Ilya V. ^{[1
]}

Lisovin, Anton V. ^{[1
]}

Nikogosov, Mikhail V. ^{[1
]}

Demidov, Oleg P. ^{[3
]}

Bang, Duong Nghia ^{[4
]}

Lam, Tran Dai ^{[5
]}

Trang, Nguyen Thi Thu ^{[5
]}

Dubonosov, Alexander D. ^{[2
]}

Minkin, Vladimir I. ^{[1
]}

机构：

[1] Southern Fed Univ, Inst Phys & Organ Chem, Rostov Na Donu 344090, Russia

[2] Russian Acad Sci, Fed Res Ctr, Southern Sci Ctr, Rostov Na Donu 344006, Russia

[3] North Caucasus Fed Univ, Stavropol 355009, Russia

[4] Minist Educ & Training, Off State Council Professorship, Hanoi 10000, Vietnam

[5] Vietnam Acad Sci & Technol, Inst Trop Technol, Hanoi 10000, Vietnam

来源：

HELIYON | 2023年 / 9卷 / 06期

基金：

俄罗斯科学基金会;

关键词：

4; 6-Di(tert-butyl)-3-nitro-1; 2-benzoquinone; o-Quinone ring expansion; Contraction of theo-quinone ring; 1; 3-Tropolones; DFT; X-ray spectroscopy; 2-METHYLQUINOLINES; ANTIBACTERIAL; CONDENSATION; DERIVATIVES;

D O I：

10.1016/j.heliyon.2023.e16943

中图分类号：

O [数理科学和化学]; P [天文学、地球科学]; Q [生物科学]; N [自然科学总论];

学科分类号：

07 ; 0710 ; 09 ;

摘要：

Condensation of quinaldine with 4,6-di (tert-butyl)-3-nitro-1,2-benzoquinone results in the for-mation of 5,7-di (tert-butyl)-2-(quinoline-2-yl)-1,3-tropolone, 5,7-di (tert-butyl)-4-nitro-2-(quin-oline-2-yl)-1,3-tropolone, 3,3-dimethyl-2-(5-hydroxy-4-nitro-3-tert-butyl-6-quinoline-2-yl-pyridine-2-yl)butanoic acid, 6-(2,2-dimethylprop-3-yl)-5-tert-butyl-4-nitro-2-(quinoline-2-yl)-pyridine-3-ol, 1,7-di (tert-butyl)-3-(quinoline-2-yl)-2-azabicyclo-[3.3.0]octa-2,7-diene-4,6-dione-N-oxide. The formation of 1,3-tropolone and pyridine-2-yl butanoic acid derivatives proceeds through a ring expansion and 2-azabicyclo [3.3.0]octa-2,7-diene-4,6-dione-N-oxide via the contraction of the o-quinone ring. The structure of the heterocyclic compounds obtained was justified by X-ray diffraction analysis, NMR spectroscopy, IR-and HRMS-spectrometry, and the proposed mechanisms of their formation include the participation of an intermediate product of the expansion reaction of the o-quinone cycle -5,7-di (tert-butyl)-4-nitro-2-(quinoline-2-yl)-cyclohepta-1,3,5-triene-1,3-diol, which was first isolated preparatively. The DFT/B3LYP/ 6-311++G** methods were used to determine the thermodynamic stability of tautomeric forms of intermediate products, as well as the relative stability of NH and OH tautomers of 5,7-di (tert- butyl)-2-(quinolin-2-yl)-1,3-tropolone and 5,7-di (tert-butyl)-4-nitro-2-(quinolin-2-yl)-1,3-tropolone.

引用

页数：14

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