Cycloaddition reactions of heterocyclic azides with 2-cyanoacetamidines as a new route to C,N-diheteroarylcarbamidines

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Cycloaddition reactions of heterocyclic azides with 2-cyanoacetamidines as a new route to C,N-diheteroarylcarbamidines. / Silaichev, Pavel S.; Beryozkina, Tetyana V.; Melekhin, Vsevolod V. et al.
In: Beilstein Journal of Organic Chemistry, Vol. 20, 2024, p. 17-24.

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

BibTeX

@article{6cacf0c56b8245179d8e272acdcfedb2,

title = "Cycloaddition reactions of heterocyclic azides with 2-cyanoacetamidines as a new route to C,N-diheteroarylcarbamidines",

abstract = "A novel and efficient base-catalyzed, transition-metal-free method for the synthesis of diheterocyclic compounds connected by an amidine linker, including apart from the common 1,2,3-triazole ring, either an additional pyrimidinedione, 4-nitroimidazole, isoxa-zole, 1,3,4-triazole, 2-oxochromone or thiazole ring, has been developed. The process was facilitated by a strong base and includes the cycloaddition reaction of 3,3-diaminoacrylonitriles (2-cyanoacetamidines) to heterocyclic azides followed by a Cornforth-type rearrangement to the final products. The reaction is tolerant to various N-monosubstituted 3,3-diaminoacrylonitriles and to different heterocyclic azides. The developed method has a broad scope and can be applied to obtain a variety of N-heteroaryl-1,2,3-triazole-4-carbimidamides with alkyl, allyl, propargyl, benzyl, cycloalkyl, and indolyl substituents at the N1 position.",

author = "Silaichev, {Pavel S.} and Beryozkina, {Tetyana V.} and Melekhin, {Vsevolod V.} and Filimonov, {Valeriy O.} and Maslivets, {Andrey N.} and Ilkin, {Vladimir G.} and Wim Dehaen and Bakulev, {Vasiliy A.}",

note = "Design and elaboration of a novel tandem process, synthesis of starting building blocks and 21-st target compounds was made by chemistry team and founded by Russian Science Foundation, project number 23-13-00248. The study of cytotoxic effect of 7 compounds was financially supported by the Ministry of Science and Higher Education of the Russian Federation within the framework of the Program of the Development of the Ural Federal University named after the first President of Russia B.N. Yeltsin under the Federal Academic Leadership Program “Priority 2030”.",

year = "2024",

doi = "10.3762/bjoc.20.3",

language = "English",

volume = "20",

pages = "17--24",

journal = "Beilstein Journal of Organic Chemistry",

issn = "1860-5397",

publisher = "Beilstein-Institut Zur Forderung der Chemischen Wissenschaften",

}

RIS

TY - JOUR

T1 - Cycloaddition reactions of heterocyclic azides with 2-cyanoacetamidines as a new route to C,N-diheteroarylcarbamidines

AU - Silaichev, Pavel S.

AU - Beryozkina, Tetyana V.

AU - Melekhin, Vsevolod V.

AU - Filimonov, Valeriy O.

AU - Maslivets, Andrey N.

AU - Ilkin, Vladimir G.

AU - Dehaen, Wim

AU - Bakulev, Vasiliy A.

N1 - Design and elaboration of a novel tandem process, synthesis of starting building blocks and 21-st target compounds was made by chemistry team and founded by Russian Science Foundation, project number 23-13-00248. The study of cytotoxic effect of 7 compounds was financially supported by the Ministry of Science and Higher Education of the Russian Federation within the framework of the Program of the Development of the Ural Federal University named after the first President of Russia B.N. Yeltsin under the Federal Academic Leadership Program “Priority 2030”.

PY - 2024

Y1 - 2024

N2 - A novel and efficient base-catalyzed, transition-metal-free method for the synthesis of diheterocyclic compounds connected by an amidine linker, including apart from the common 1,2,3-triazole ring, either an additional pyrimidinedione, 4-nitroimidazole, isoxa-zole, 1,3,4-triazole, 2-oxochromone or thiazole ring, has been developed. The process was facilitated by a strong base and includes the cycloaddition reaction of 3,3-diaminoacrylonitriles (2-cyanoacetamidines) to heterocyclic azides followed by a Cornforth-type rearrangement to the final products. The reaction is tolerant to various N-monosubstituted 3,3-diaminoacrylonitriles and to different heterocyclic azides. The developed method has a broad scope and can be applied to obtain a variety of N-heteroaryl-1,2,3-triazole-4-carbimidamides with alkyl, allyl, propargyl, benzyl, cycloalkyl, and indolyl substituents at the N1 position.

AB - A novel and efficient base-catalyzed, transition-metal-free method for the synthesis of diheterocyclic compounds connected by an amidine linker, including apart from the common 1,2,3-triazole ring, either an additional pyrimidinedione, 4-nitroimidazole, isoxa-zole, 1,3,4-triazole, 2-oxochromone or thiazole ring, has been developed. The process was facilitated by a strong base and includes the cycloaddition reaction of 3,3-diaminoacrylonitriles (2-cyanoacetamidines) to heterocyclic azides followed by a Cornforth-type rearrangement to the final products. The reaction is tolerant to various N-monosubstituted 3,3-diaminoacrylonitriles and to different heterocyclic azides. The developed method has a broad scope and can be applied to obtain a variety of N-heteroaryl-1,2,3-triazole-4-carbimidamides with alkyl, allyl, propargyl, benzyl, cycloalkyl, and indolyl substituents at the N1 position.

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UR - http://www.scopus.com/inward/record.url?partnerID=8YFLogxK&scp=85186067011

U2 - 10.3762/bjoc.20.3

DO - 10.3762/bjoc.20.3

M3 - Article

VL - 20

SP - 17

EP - 24

JO - Beilstein Journal of Organic Chemistry

JF - Beilstein Journal of Organic Chemistry

SN - 1860-5397

ER -

ID: 52350396