Three-component synthesis of bridged 1,3,5-triazinanes

被引：0

作者：

Podrezova, Alexandra G. ^{[1
]}

Grudova, Mariya V. ^{[2
]}

Khrustalev, Victor N. ^{[1
,2
]}

Kvyatkovskaya, Elizaveta A. ^{[1
]}

Nikitina, Eugeniya V. ^{[1
]}

Brazhkin, Vadim V. ^{[3
]}

Zubkov, Fedor I. ^{[1
]}

机构：

[1] RUDN Univ, Peoples Friendship Univ Russia, 6 Miklukho Maklaya St, Moscow 117198, Russia

[2] RAS, Zelinsky Inst Organ Chem, 47 Leninsky Prospect, Moscow 119991, Russia

[3] Russian Acad Sci, Vereshchagin Inst High Pressure Phys, Kaluzhskoe Shosse 14, Troitsk 108840, Moscow, Russia

来源：

TETRAHEDRON | 2024年 / 150卷

关键词：

Three -component reaction; 5-Triazinanes; Bicycles; 5-triazabicyclo[3.2.1]octane; 5-triazabicyclo[3.3.1]nonane; 8-triazabicyclo[4.3.1]decane; ACIDITIES; ACIDS; BENZENESULFONAMIDES; FORMALDEHYDE;

D O I：

10.1016/j.tet.2023.133750

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient one-pot procedure has been developed for the synthesis of bridged 1,3,5-triazinanes, unexplored classes of heterocyclic polydentate scaffolds. By means of a pseudo five-component reaction between primary diamines (ethylenediamine, 1,3-propylenediamine, 1,4-butylenediamine), sulfonamides, and three equivalents of paraformaldehyde, a broad series of 1,3,5-triazabicyco[3.2.1]octanes, 1,3,5-triazabicyco[3.3.1]nonanes and 1,6,8-triazobicyclo[4.3.1]decanes were prepared. Boiling chloroform and an additive of Mg(ClO4)(2) were shown to be the most efficient conditions for the condensation. Putrescine is probably the longest diamine which can be involved in this protocol. It was demonstrated that cadaverine was unsuitable for preparation of corresponding 1,7,9-triazabicyclo[5.3.1]undecanes. The structure of all classes of the obtained azabicycles was elucidated by XRD analysis.

引用

页数：9

共 25 条

[1] THE STRENGTH OF HETEROCYCLIC BASES [J].

ALBERT, A ;

GOLDACRE, R ;

PHILLIPS, J .

JOURNAL OF THE CHEMICAL SOCIETY, 1948, (DEC) :2240-2249

[2] EQUILIBRIUM ACIDITIES IN DIMETHYL-SULFOXIDE SOLUTION [J].

BORDWELL, FG .

ACCOUNTS OF CHEMICAL RESEARCH, 1988, 21 (12) :456-463

[3] ACIDITIES OF CARBOXAMIDES, HYDROXAMIC ACIDS, CARBOHYDRAZIDES, BENZENESULFONAMIDES, AND BENZENESULFONOHYDRAZIDES IN DMSO SOLUTION [J].

BORDWELL, FG ;

FRIED, HE ;

HUGHES, DL ;

LYNCH, TY ;

SATISH, AV ;

WHANG, YE .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (10) :3330-3336

[4] ACIDITIES OF ANILINES AND TOLUENES [J].

BORDWELL, FG ;

ALGRIM, D ;

VANIER, NR .

JOURNAL OF ORGANIC CHEMISTRY, 1977, 42 (10) :1817-1819

[5] THE ACIDITY OF WEAK CARBON ACIDS .5. THE KINETIC ACIDITIES OF SUBSTITUTED BENZYL CYANIDES USING SUBSTITUTED BENZYLAMINES AS BASES [J].

BOWDEN, K ;

HIRANI, SIJ .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1990, (11) :1889-1891

[6]

Braude E.A., 1955, Determination of Organic Structures by Physical Methods, DOI [10.1016/C2013-0-12413-0, DOI 10.1016/C2013-0-12413-0]

[7] CORRELATION OF THE BASE STRENGTHS OF AMINES [J].

HALL, HK .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1957, 79 (20) :5441-5444

[8]

Kireeva DR, 2022, RUSS J GEN CHEM+, V92, P24, DOI [10.31857/S0044460X22010061, 10.1134/S1070363222010054]

[9] Raise the anchor! Synthesis, X-ray and NMR characterization of 1,3,5-triazinanes with an axial tert-butyl group [J].

Kletskov, Alexey V. ;

Zatykina, Anastasya D. ;

Grudova, Mariya V. ;

Sinelshchikova, Anna A. ;

Grigoriev, Mikhail S. ;

Zaytsev, Vladimir P. ;

Gil, Diego M. ;

Novikov, Roman A. ;

Zubkov, Fedor I. ;

Frontera, Antonio .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2020, 18 (41) :8386-8394

[10] Straightforward Three-Component Synthesis of N′,N′′-Disubstituted N -Alkyl-1,3,5-Triazinanes [J].

Kletskov, Alexey V. ;

Frontera, Antonio ;

Sinelshchikova, Anna A. ;

Grigoriev, Mikhail S. ;

Zaytsev, Vladimir P. ;

Grudova, Mariya V. ;

Bunev, Alexander S. ;

Presnukhina, Sofia ;

Shetnev, Anton ;

Zubkov, Fedor I. .

SYNLETT, 2020, 31 (11) :1067-1072

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