Concise Approach towards Tetramic Acid Derivatives via Ugi Reaction/Dieckmann Cyclization Sequence

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Concise Approach towards Tetramic Acid Derivatives via Ugi Reaction/Dieckmann Cyclization Sequence. / Гуранова, Наталья Игоревна ; Бакулина, Ольга Юрьевна; Кантин, Григорий Павлович; Дарьин, Дмитрий Викторович.

In: ChemistrySelect, Vol. 9, No. 8, e202303869, 22.02.2024.

Research output: Contribution to journal › Article › peer-review

BibTeX

@article{7f2bbd416c354b4994cbeb1acc395e67,

title = "Concise Approach towards Tetramic Acid Derivatives via Ugi Reaction/Dieckmann Cyclization Sequence",

abstract = "Tetramic acids exhibit intriguing biological activity and are particularly attractive scaffolds for drug design. In this paper, we present a convenient approach based on the Dieckmann cyclization of Ugi adducts of malonic monoesters to afford a series of medically important polysubstituted tetramic acid derivatives. This simple and versatile method tolerates various substituents in both the amine, aldehyde and isocyanide moieties allowing the use of α-substituted malonic acid monoesters. Examples of further functionalization of the free methylene group in the synthesized compounds have been presented.",

keywords = "Dieckmann condensation, MCR, Ugi reaction, pyrrolidine-2,4-dione, tetramic acid",

author = "Гуранова, {Наталья Игоревна} and Бакулина, {Ольга Юрьевна} and Кантин, {Григорий Павлович} and Дарьин, {Дмитрий Викторович}",

year = "2024",

month = feb,

day = "22",

doi = "10.1002/slct.202303869",

language = "English",

volume = "9",

journal = "ChemistrySelect",

issn = "2365-6549",

publisher = "Wiley-Blackwell",

number = "8",

}

RIS

TY - JOUR

T1 - Concise Approach towards Tetramic Acid Derivatives via Ugi Reaction/Dieckmann Cyclization Sequence

AU - Гуранова, Наталья Игоревна

AU - Бакулина, Ольга Юрьевна

AU - Кантин, Григорий Павлович

AU - Дарьин, Дмитрий Викторович

PY - 2024/2/22

Y1 - 2024/2/22

N2 - Tetramic acids exhibit intriguing biological activity and are particularly attractive scaffolds for drug design. In this paper, we present a convenient approach based on the Dieckmann cyclization of Ugi adducts of malonic monoesters to afford a series of medically important polysubstituted tetramic acid derivatives. This simple and versatile method tolerates various substituents in both the amine, aldehyde and isocyanide moieties allowing the use of α-substituted malonic acid monoesters. Examples of further functionalization of the free methylene group in the synthesized compounds have been presented.

AB - Tetramic acids exhibit intriguing biological activity and are particularly attractive scaffolds for drug design. In this paper, we present a convenient approach based on the Dieckmann cyclization of Ugi adducts of malonic monoesters to afford a series of medically important polysubstituted tetramic acid derivatives. This simple and versatile method tolerates various substituents in both the amine, aldehyde and isocyanide moieties allowing the use of α-substituted malonic acid monoesters. Examples of further functionalization of the free methylene group in the synthesized compounds have been presented.

KW - Dieckmann condensation

KW - MCR

KW - Ugi reaction

KW - pyrrolidine-2,4-dione

KW - tetramic acid

UR - https://www.mendeley.com/catalogue/62dd3474-1e49-35d6-bb79-59833e9c8afc/

U2 - 10.1002/slct.202303869

DO - 10.1002/slct.202303869

M3 - Article

VL - 9

JO - ChemistrySelect

JF - ChemistrySelect

SN - 2365-6549

IS - 8

M1 - e202303869

ER -

ID: 117255162