Metal-free Three-Component Synthesis of 1,2,3-Triazoline-4-sulfonamides

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Metal-free Three-Component Synthesis of 1,2,3-Triazoline-4-sulfonamides. / Bubyrev, Andrey ; Adamchik, Maria ; Dar'In, Dmitry ; Kantin, Grigory ; Krasavin, Mikhail.

In: Journal of Organic Chemistry, Vol. 86, No. 19, 01.10.2021, p. 13454–13464.

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

BibTeX

@article{1973e76112ee4dcca2c93a80f868436f,

title = "Metal-free Three-Component Synthesis of 1,2,3-Triazoline-4-sulfonamides",

abstract = "A new type of diazo compounds, namely, CH-diazomethane sulfonamides (generated in situ from readily available α-acetyl-α-diazomethane sulfonamides), was employed in a 1,3-dipolar cycloaddition reaction with imines (also formed in situ from primary amines and aldehydes). The reaction gave hitherto undescribed 1,5-disubstituted 1,2,3-triazoline-4-sulfonamides, which were obtained in good to excellent yields with complete trans diastereoselectivity. These new sulfonamides based on the nonaromatic 1,2,3-triazoline core are rather attractive from a medicinal chemistry standpoint in light of the strong emphasis recently put on the nonflat, more saturated (higher Fsp3) scaffolds for lead-generation libraries. The oxidative aromatization of 1,2,3-triazoline-4-sulfonamides by manganese(IV) oxide gave nearly quantitative yields of 1,2,3-triazole-4-sulfonamides, of which only two examples have been reported in the literature. ",

keywords = "DIELS-ALDER REACTIONS, TRIAZOLINES, POTENT, DERIVATIVES, REACTIVITY, DISCOVERY, AZIDE",

author = "Andrey Bubyrev and Maria Adamchik and Dmitry Dar'In and Grigory Kantin and Mikhail Krasavin",

note = "Publisher Copyright: {\textcopyright} 2021 American Chemical Society.",

year = "2021",

month = oct,

day = "1",

doi = "10.1021/acs.joc.1c01552",

language = "English",

volume = "86",

pages = "13454–13464",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

number = "19",

}

RIS

TY - JOUR

T1 - Metal-free Three-Component Synthesis of 1,2,3-Triazoline-4-sulfonamides

AU - Bubyrev, Andrey

AU - Adamchik, Maria

AU - Dar'In, Dmitry

AU - Kantin, Grigory

AU - Krasavin, Mikhail

PY - 2021/10/1

Y1 - 2021/10/1

N2 - A new type of diazo compounds, namely, CH-diazomethane sulfonamides (generated in situ from readily available α-acetyl-α-diazomethane sulfonamides), was employed in a 1,3-dipolar cycloaddition reaction with imines (also formed in situ from primary amines and aldehydes). The reaction gave hitherto undescribed 1,5-disubstituted 1,2,3-triazoline-4-sulfonamides, which were obtained in good to excellent yields with complete trans diastereoselectivity. These new sulfonamides based on the nonaromatic 1,2,3-triazoline core are rather attractive from a medicinal chemistry standpoint in light of the strong emphasis recently put on the nonflat, more saturated (higher Fsp3) scaffolds for lead-generation libraries. The oxidative aromatization of 1,2,3-triazoline-4-sulfonamides by manganese(IV) oxide gave nearly quantitative yields of 1,2,3-triazole-4-sulfonamides, of which only two examples have been reported in the literature.

AB - A new type of diazo compounds, namely, CH-diazomethane sulfonamides (generated in situ from readily available α-acetyl-α-diazomethane sulfonamides), was employed in a 1,3-dipolar cycloaddition reaction with imines (also formed in situ from primary amines and aldehydes). The reaction gave hitherto undescribed 1,5-disubstituted 1,2,3-triazoline-4-sulfonamides, which were obtained in good to excellent yields with complete trans diastereoselectivity. These new sulfonamides based on the nonaromatic 1,2,3-triazoline core are rather attractive from a medicinal chemistry standpoint in light of the strong emphasis recently put on the nonflat, more saturated (higher Fsp3) scaffolds for lead-generation libraries. The oxidative aromatization of 1,2,3-triazoline-4-sulfonamides by manganese(IV) oxide gave nearly quantitative yields of 1,2,3-triazole-4-sulfonamides, of which only two examples have been reported in the literature.

KW - DIELS-ALDER REACTIONS

KW - TRIAZOLINES

KW - POTENT

KW - DERIVATIVES

KW - REACTIVITY

KW - DISCOVERY

KW - AZIDE

UR - http://www.scopus.com/inward/record.url?scp=85115921740&partnerID=8YFLogxK

U2 - 10.1021/acs.joc.1c01552

DO - 10.1021/acs.joc.1c01552

M3 - Article

AN - SCOPUS:85115921740

VL - 86

SP - 13454

EP - 13464

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

SN - 0022-3263

IS - 19

ER -

ID: 86412882