Facile access to 3-sulfonylquinolines via Knoevenagel condensation/aza-Wittig reaction cascade involving ortho -azidobenzaldehydes and β-ketosulfonamides and sulfones

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Facile access to 3-sulfonylquinolines via Knoevenagel condensation/aza-Wittig reaction cascade involving ortho -azidobenzaldehydes and β-ketosulfonamides and sulfones. / Малкова, Ксения Павловна ; Бубырев, Андрей Иванович ; Калинин, Станислав Алексеевич ; Дарьин, Дмитрий Викторович.

In: Beilstein Journal of Organic Chemistry, Vol. 19, 09.06.2023, p. 800-807.

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

BibTeX

@article{a4b1ff34131c4b6c8fb289ff00224fa7,

title = "Facile access to 3-sulfonylquinolines via Knoevenagel condensation/aza-Wittig reaction cascade involving ortho -azidobenzaldehydes and β-ketosulfonamides and sulfones",

abstract = "Quinoline-based sulfonyl derivatives, and especially sulfonamides, are relevant and promising structures for drug design. We have developed a new convenient protocol for the synthesis of 3-sulfonyl-substituted quinolines (sulfonamides and sulfones). The approach is based on a Knoevenagel condensation/aza-Wittig reaction cascade involving o-azidobenzaldehydes and ketosulfonamides or ketosulfones as key building blocks. The protocol is appropriate for both ketosulfonyl reagents and α-sulfonyl-substituted alkyl acetates providing the target quinoline derivatives in good to excellent yields. ",

keywords = "aza-Wittig reaction, azides, cyclocondensation, quinolones, sulfonamides",

author = "Малкова, {Ксения Павловна} and Бубырев, {Андрей Иванович} and Калинин, {Станислав Алексеевич} and Дарьин, {Дмитрий Викторович}",

year = "2023",

month = jun,

day = "9",

doi = "10.3762/bjoc.19.60",

language = "English",

volume = "19",

pages = "800--807",

journal = "Beilstein Journal of Organic Chemistry",

issn = "1860-5397",

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

}

RIS

TY - JOUR

T1 - Facile access to 3-sulfonylquinolines via Knoevenagel condensation/aza-Wittig reaction cascade involving ortho -azidobenzaldehydes and β-ketosulfonamides and sulfones

AU - Малкова, Ксения Павловна

AU - Бубырев, Андрей Иванович

AU - Калинин, Станислав Алексеевич

AU - Дарьин, Дмитрий Викторович

PY - 2023/6/9

Y1 - 2023/6/9

N2 - Quinoline-based sulfonyl derivatives, and especially sulfonamides, are relevant and promising structures for drug design. We have developed a new convenient protocol for the synthesis of 3-sulfonyl-substituted quinolines (sulfonamides and sulfones). The approach is based on a Knoevenagel condensation/aza-Wittig reaction cascade involving o-azidobenzaldehydes and ketosulfonamides or ketosulfones as key building blocks. The protocol is appropriate for both ketosulfonyl reagents and α-sulfonyl-substituted alkyl acetates providing the target quinoline derivatives in good to excellent yields.

AB - Quinoline-based sulfonyl derivatives, and especially sulfonamides, are relevant and promising structures for drug design. We have developed a new convenient protocol for the synthesis of 3-sulfonyl-substituted quinolines (sulfonamides and sulfones). The approach is based on a Knoevenagel condensation/aza-Wittig reaction cascade involving o-azidobenzaldehydes and ketosulfonamides or ketosulfones as key building blocks. The protocol is appropriate for both ketosulfonyl reagents and α-sulfonyl-substituted alkyl acetates providing the target quinoline derivatives in good to excellent yields.

KW - aza-Wittig reaction

KW - azides

KW - cyclocondensation

KW - quinolones

KW - sulfonamides

UR - https://www.mendeley.com/catalogue/1d0f43d5-aa7b-392c-90cb-18a3b87d48f8/

U2 - 10.3762/bjoc.19.60

DO - 10.3762/bjoc.19.60

M3 - Article

C2 - 37346493

VL - 19

SP - 800

EP - 807

JO - Beilstein Journal of Organic Chemistry

JF - Beilstein Journal of Organic Chemistry

SN - 1860-5397

ER -

ID: 108471179