Extending the scope of the new variant of the Castagnoli-Cushman cyclocondensation onto o-methyl benzoic acids bearing various electron-withdrawing groups in the α-position

Standard

Extending the scope of the new variant of the Castagnoli-Cushman cyclocondensation onto o-methyl benzoic acids bearing various electron-withdrawing groups in the α-position. / Гуранова, Наталья Игоревна ; Яковлева, Людмила Вадимовна ; Бакулина, Ольга Юрьевна ; Дарьин, Дмитрий Викторович ; Красавин, Михаил Юрьевич.

In: Molecules, Vol. 27, No. 21, 7211, 11.2022.

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

BibTeX

@article{7d362cfd44fa4afbbae9d18648e90d42,

title = "Extending the scope of the new variant of the Castagnoli-Cushman cyclocondensation onto o-methyl benzoic acids bearing various electron-withdrawing groups in the α-position",

abstract = "Based on the previously reported involvement of homophthalic acid monoesters in the Castagnoli–Cushman reaction-type cyclocondensation with imines, we tested a number of other o-methyl benzoic acids bearing various electron-withdrawing groups in the α-position. The majority of these substrates delivered the expected tetrahydroisoquinolone adducts on activation with CDI or acetic anhydride. Homophthalic acid mononitriles displayed the highest promise as substrates for the new reaction, both in terms of scope and product yields. Homophthalic acid monoamides either gave low yields or failed to react with imines. Sulfonyl-substituted substrates gave the desired (and hitherto unknown) type of tetrahydroisoquinolines. Despite the low yields, this approach to sulfonyl-substituted tetrahydroisoquinolines appears practical as alternative syntheses based on the traditional, carboxylic acid CCR adducts would presumably be cumbersome and multistep. The azido- and nitro-substituted o-methyl benzoic acids failed to react with imines.",

keywords = "Castagnoli-Cushman reaction, cyclocondensation, homophthalic, imine, isoquionolone, Benzoates, Imines, Tetrahydroisoquinolines, Electrons",

author = "Гуранова, {Наталья Игоревна} and Яковлева, {Людмила Вадимовна} and Бакулина, {Ольга Юрьевна} and Дарьин, {Дмитрий Викторович} and Красавин, {Михаил Юрьевич}",

note = "Publisher Copyright: {\textcopyright} 2022 by the authors.",

year = "2022",

month = nov,

doi = "10.3390/molecules27217211",

language = "English",

volume = "27",

journal = "Molecules",

issn = "1420-3049",

publisher = "MDPI AG",

number = "21",

}

RIS

TY - JOUR

T1 - Extending the scope of the new variant of the Castagnoli-Cushman cyclocondensation onto o-methyl benzoic acids bearing various electron-withdrawing groups in the α-position

AU - Гуранова, Наталья Игоревна

AU - Яковлева, Людмила Вадимовна

AU - Бакулина, Ольга Юрьевна

AU - Дарьин, Дмитрий Викторович

AU - Красавин, Михаил Юрьевич

PY - 2022/11

Y1 - 2022/11

N2 - Based on the previously reported involvement of homophthalic acid monoesters in the Castagnoli–Cushman reaction-type cyclocondensation with imines, we tested a number of other o-methyl benzoic acids bearing various electron-withdrawing groups in the α-position. The majority of these substrates delivered the expected tetrahydroisoquinolone adducts on activation with CDI or acetic anhydride. Homophthalic acid mononitriles displayed the highest promise as substrates for the new reaction, both in terms of scope and product yields. Homophthalic acid monoamides either gave low yields or failed to react with imines. Sulfonyl-substituted substrates gave the desired (and hitherto unknown) type of tetrahydroisoquinolines. Despite the low yields, this approach to sulfonyl-substituted tetrahydroisoquinolines appears practical as alternative syntheses based on the traditional, carboxylic acid CCR adducts would presumably be cumbersome and multistep. The azido- and nitro-substituted o-methyl benzoic acids failed to react with imines.

AB - Based on the previously reported involvement of homophthalic acid monoesters in the Castagnoli–Cushman reaction-type cyclocondensation with imines, we tested a number of other o-methyl benzoic acids bearing various electron-withdrawing groups in the α-position. The majority of these substrates delivered the expected tetrahydroisoquinolone adducts on activation with CDI or acetic anhydride. Homophthalic acid mononitriles displayed the highest promise as substrates for the new reaction, both in terms of scope and product yields. Homophthalic acid monoamides either gave low yields or failed to react with imines. Sulfonyl-substituted substrates gave the desired (and hitherto unknown) type of tetrahydroisoquinolines. Despite the low yields, this approach to sulfonyl-substituted tetrahydroisoquinolines appears practical as alternative syntheses based on the traditional, carboxylic acid CCR adducts would presumably be cumbersome and multistep. The azido- and nitro-substituted o-methyl benzoic acids failed to react with imines.

KW - Castagnoli-Cushman reaction

KW - cyclocondensation

KW - homophthalic

KW - imine

KW - isoquionolone

KW - Benzoates

KW - Imines

KW - Tetrahydroisoquinolines

KW - Electrons

UR - http://www.scopus.com/inward/record.url?scp=85141637474&partnerID=8YFLogxK

UR - https://www.mendeley.com/catalogue/931c096b-8b0c-3d03-be25-4d8a765b9203/

U2 - 10.3390/molecules27217211

DO - 10.3390/molecules27217211

M3 - Article

C2 - 36364037

VL - 27

JO - Molecules

JF - Molecules

SN - 1420-3049

IS - 21

M1 - 7211

ER -

ID: 100702201