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@article{7d38e8c62b934a0b8cc7a1087531b973,
title = "Blue Light Induced N-H Functionalization of Tetrazoles with Aryldiazoacetates: Access to 1,5-disubstituted Regioisomers",
abstract = "A novel method for synthesizing 1,5-disubstituted tetrazole derivatives via blue light-promoted N–H insertion of aryldiazoacetates into NH-tetrazoles is presented. The reaction affords mixtures of regioisomeric products, with a predominance of 1,5-disubstituted derivatives. A comprehensive investigation of reaction conditions and substrate effects influencing regioselectivity has been performed. These findings provide new insights into the regioselectivity of NH-tetrazole alkylation and reveal potential applications of this approach in the assembly of tetrazole-containing scaffolds.",
keywords = "N-alkylation, N–H insertion reaction, diazocarbonyl compounds, regioselectivity, tetrazoles",
author = "Радюпов, {Валентин Эдуардович} and Кантин, {Григорий Павлович} and Мешалкин, {Степан Алексеевич} and Тупикина, {Елена Юрьевна} and Дарьин, {Дмитрий Викторович}",
year = "2026",
month = apr,
day = "1",
doi = "10.1055/a-2837-6310",
language = "English",
journal = "Synthesis",
issn = "0039-7881",
publisher = "Georg Thieme Verlag",

}

RIS

TY - JOUR

T1 - Blue Light Induced N-H Functionalization of Tetrazoles with Aryldiazoacetates: Access to 1,5-disubstituted Regioisomers

AU - Радюпов, Валентин Эдуардович

AU - Кантин, Григорий Павлович

AU - Мешалкин, Степан Алексеевич

AU - Тупикина, Елена Юрьевна

AU - Дарьин, Дмитрий Викторович

PY - 2026/4/1

Y1 - 2026/4/1

N2 - A novel method for synthesizing 1,5-disubstituted tetrazole derivatives via blue light-promoted N–H insertion of aryldiazoacetates into NH-tetrazoles is presented. The reaction affords mixtures of regioisomeric products, with a predominance of 1,5-disubstituted derivatives. A comprehensive investigation of reaction conditions and substrate effects influencing regioselectivity has been performed. These findings provide new insights into the regioselectivity of NH-tetrazole alkylation and reveal potential applications of this approach in the assembly of tetrazole-containing scaffolds.

AB - A novel method for synthesizing 1,5-disubstituted tetrazole derivatives via blue light-promoted N–H insertion of aryldiazoacetates into NH-tetrazoles is presented. The reaction affords mixtures of regioisomeric products, with a predominance of 1,5-disubstituted derivatives. A comprehensive investigation of reaction conditions and substrate effects influencing regioselectivity has been performed. These findings provide new insights into the regioselectivity of NH-tetrazole alkylation and reveal potential applications of this approach in the assembly of tetrazole-containing scaffolds.

KW - N-alkylation

KW - N–H insertion reaction

KW - diazocarbonyl compounds

KW - regioselectivity

KW - tetrazoles

UR - https://www.mendeley.com/catalogue/cf625014-4293-3caa-ba1e-6389562d4756/

U2 - 10.1055/a-2837-6310

DO - 10.1055/a-2837-6310

M3 - Article

JO - Synthesis

JF - Synthesis

SN - 0039-7881

ER -

ID: 151787739