Intramolecular Cyclization of the ortho-Substituted N-arylquinone Imines under Basic and Thermal Conditions

被引：1

作者：

Khodykina, Evgenia S. ^{[1
]}

Steglenko, Dmitry V. ^{[1
]}

Vetrova, Elena V. ^{[1
]}

Pugachev, Artem D. ^{[1
]}

Galkina, Maria S. ^{[1
]}

Borodkina, Inna G. ^{[1
]}

Lesin, Alexander V. ^{[1
]}

Demidov, Oleg P. ^{[2
]}

Metelitsa, Anatoly V. ^{[1
]}

Kolodina, Alexandra A. ^{[1
]}

机构：

[1] Southern Fed Univ, Inst Phys & Organ Chem, 194-2 Stachki St, Rostov Na Donu 344090, Russia

[2] North Caucasus Fed Univ, Dept Chem, Inst Math & Nat Sci, 1a Pushkina St, Stavropol 355009, Russia

来源：

CHEMISTRYSELECT | 2023年 / 8卷 / 03期

关键词：

N-arylquinone imines; benzazines; benzazoles; cyclization; spiro compounds; DERIVATIVES; STEREODYNAMICS; TAUTOMERISM; INDOPHENOLS; AMIDINES; ANALOGS; BENZIMIDAZOLE;

D O I：

10.1002/slct.202204317

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The S(O,N)-benzyl ethers of N-arylquinone imines undergo cyclization under the action of bases to form products of the benzothiazol, benzoxazole, and benzimidazole series, while under thermal conditions they undergo a non-catalyzed rearrangement to form spiro-cyclohexadiene derivatives of benzazines. The benzimidazole, spirobenzothiazine, and spirobenzoxazine structures were supported by the x-ray diffraction method. The possibility of intramolecular photochemical cyclization was investigated; ortho-S(O,N)-benzyl-substituted N-arylquinone imines show high photostability under UV irradiation. The features of the cyclization processes of quinone imine derivatives were revealed by DFT calculations using the wB97XD/6-311++G** method.

引用

页数：10

共 39 条

[1] Intramolecular Cyclization of ortho-Substituted Chalcones in the Presence of Palladium Complexes with Chiral Bisphosphine Ligands
M. A. Ashatkina
A. N. Reznikov
Yu. N. Klimochkin
Russian Journal of Organic Chemistry, 2022, 58 : 710 - 719
[2] Intramolecular Cyclization of ortho-Substituted Chalcones in the Presence of Palladium Complexes with Chiral Bisphosphine Ligands
Ashatkina, M. A.
Reznikov, A. N.
Klimochkin, Yu N.
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2022, 58 (05) : 710 - 719
[3] Synthesis of fused pyrazoles via intramolecular cyclization of appropriately ortho-substituted nitroarenes and nitroheteroarenes
Remennikov, Grigoriy Ya.
CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2017, 53 (02) : 101 - 115
[4] Synthesis of fused pyrazoles via intramolecular cyclization of appropriately ortho-substituted nitroarenes and nitroheteroarenes
Grigoriy Ya. Remennikov
Chemistry of Heterocyclic Compounds, 2017, 53 : 101 - 115
[5] INTRAMOLECULAR HYDROGEN-BONDING IN ORTHO-SUBSTITUTED N,N-DIMETHYLBENZAMIDES
FONG, CW
AUSTRALIAN JOURNAL OF CHEMISTRY, 1980, 33 (06) : 1285 - 1290
[6] CONVERSIONS OF ORTHO-SUBSTITUTED NITROSOPHENYLCYCLOPROPANES, NITROPHENYLCYCLOPROPANES AND AZIDOPHENYLCYCLOPROPANES UNDER THE CONDITIONS OF NITRENE GENERATION
MOCHALOV, SS
FEDOTOV, AN
SIZOV, AI
SHABAROV, YS
ZHURNAL ORGANICHESKOI KHIMII, 1979, 15 (07): : 1425 - 1431
[7] Intramolecular Hydrogen Bonding in ortho-Substituted Arylamide Oligomers: A Computational and Experimental Study of ortho-Fluoro- and ortho-Chloro-N-methylbenzamides
Galan, Jhenny F.
Brown, Jodian
Wildin, Jayme L.
Liu, Zhiwei
Liu, Dahui
Moyna, Guillermo
Pophristic, Vojislava
JOURNAL OF PHYSICAL CHEMISTRY B, 2009, 113 (38): : 12809 - 12815
[8] CYCLIZATION OF ORTHO-SUBSTITUTED N-ARYLBENZIMIDOYL NITRENES .2. PREFERENTIAL CYCLIZATIONS AT AN ORTHO-POSITION BEARING A METHOXYCARBONYL GROUP
GILCHRIST, TL
GORDON, PF
PIPE, DF
REES, CW
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1979, (09): : 2303 - 2307
[9] Selective Synthesis of ortho-Substituted Diarylsulfones by Using NHC-Au Catalysts under Mild Conditions
Zhu, Haibo
Shen, Yajing
Wen, Daheng
Le, Zhang-Gao
Tu, Tao
ORGANIC LETTERS, 2019, 21 (04) : 974 - 979
[10] THERMAL AND ACID-CATALYZED REARRANGEMENT OF ORTHO-SUBSTITUTED N-(ALPHA-METHYLALLYL)-ANILINES
JOLIDON, S
HANSEN, HJ
CHIMIA, 1976, 30 (01) : 23 - 25

← 1 2 3 4 →