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

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

Журнал

Tetrahedron
ISSN: 0040-4020 , E-ISSN: 1464-5416

Вых. Данные

Год: 2024, Том: 150, Номер статьи : 133750, Страниц : DOI: 10.1016/j.tet.2023.133750

Авторы

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

Организации

1	Peoples' Friendship University of Russia (RUDN University), 6 Miklukho-Maklaya Street, Moscow, 117198, Russian Federation
2	Zelinsky Institute of Organic Chemistry of RAS, 47 Leninsky Prospect, 119991, Moscow, Russian Federation
3	Vereshchagin Institute for High Pressure Physics, Russian Academy of Sciences, Kaluzhskoe Shosse 14, 108840, Troitsk, Moscow, Russian Federation

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 сadaverine 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.

Podrezova A.G. , Grudova M.V. , Khrustalev V.N. , Kvyatkovskaya E.A. , Nikitina E.V. , Brazhkin V.V. , Zubkov F.I.
Three-component synthesis of bridged 1,3,5-triazinanes
Tetrahedron. 2024. V.150. 133750 . DOI: 10.1016/j.tet.2023.133750 WOS Scopus OpenAlex

Web of science:	WOS:001168426000001
Scopus:	2-s2.0-85177567351
OpenAlex:	W4388639803

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