New reagent space and new scope for the Castagnoli-Cushman reaction of oximes and 3-arylglutaconic anhydrides

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New reagent space and new scope for the Castagnoli-Cushman reaction of oximes and 3-arylglutaconic anhydrides. / Банных, Антон Викторович ; Левашова, Екатерина Юрьевна ; Бакулина, Ольга Юрьевна ; Красавин, Михаил Юрьевич.

In: Organic and Biomolecular Chemistry, Vol. 86, No. 44, 16.11.2022, p. 8643-8648.

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

BibTeX

@article{2e55e670737f4c91bd5779063de8c9e2,

title = "New reagent space and new scope for the Castagnoli-Cushman reaction of oximes and 3-arylglutaconic anhydrides",

abstract = "The Castagnoli-Cushman reaction of oximes, discovered originally for homophthalic anhydride, stimulated the search for other cyclic anhydrides that would be workable in that reaction. Finally, 3-arylglutaconic acid anhydrides were identified as displaying the right reactivity towards a wide range of oximes (including those which did not react with homophthalic anhydride, such as derivatives of aliphatic aldehydes or ketones and substrates with nucleophilic side groups) and delivering, after 18 h at 110 °C in DMSO, β,γ-unsaturated N-hydroxylactam products lacking the carboxylic acid functionality as the result of decarboxylation accompanying the cyclocondensation process. The reaction was found to be scalable to gram quantities of the starting anhydrides. The products were shown to be easily amenable to post-condensational double-bond transposition or reduction. As expected from cyclic hydroxamic acids, the reaction products were shown to bind Fe(iii) and Cu(ii) ions (selectively out of a panel of 16 metal cations) and potentially serve as fluorescent metal sensors.",

keywords = "Anhydrides/chemistry, Ferric Compounds/chemistry, Hydroxamic Acids/chemistry, Indicators and Reagents, Oximes/chemistry",

author = "Банных, {Антон Викторович} and Левашова, {Екатерина Юрьевна} and Бакулина, {Ольга Юрьевна} and Красавин, {Михаил Юрьевич}",

note = "Publisher Copyright: {\textcopyright} 2022 The Royal Society of Chemistry.",

year = "2022",

month = nov,

day = "16",

doi = "10.1039/d2ob01675c",

language = "English",

volume = "86",

pages = "8643--8648",

journal = "Organic and Biomolecular Chemistry",

issn = "1477-0520",

publisher = "Royal Society of Chemistry",

number = "44",

}

RIS

TY - JOUR

T1 - New reagent space and new scope for the Castagnoli-Cushman reaction of oximes and 3-arylglutaconic anhydrides

AU - Банных, Антон Викторович

AU - Левашова, Екатерина Юрьевна

AU - Бакулина, Ольга Юрьевна

AU - Красавин, Михаил Юрьевич

PY - 2022/11/16

Y1 - 2022/11/16

N2 - The Castagnoli-Cushman reaction of oximes, discovered originally for homophthalic anhydride, stimulated the search for other cyclic anhydrides that would be workable in that reaction. Finally, 3-arylglutaconic acid anhydrides were identified as displaying the right reactivity towards a wide range of oximes (including those which did not react with homophthalic anhydride, such as derivatives of aliphatic aldehydes or ketones and substrates with nucleophilic side groups) and delivering, after 18 h at 110 °C in DMSO, β,γ-unsaturated N-hydroxylactam products lacking the carboxylic acid functionality as the result of decarboxylation accompanying the cyclocondensation process. The reaction was found to be scalable to gram quantities of the starting anhydrides. The products were shown to be easily amenable to post-condensational double-bond transposition or reduction. As expected from cyclic hydroxamic acids, the reaction products were shown to bind Fe(iii) and Cu(ii) ions (selectively out of a panel of 16 metal cations) and potentially serve as fluorescent metal sensors.

AB - The Castagnoli-Cushman reaction of oximes, discovered originally for homophthalic anhydride, stimulated the search for other cyclic anhydrides that would be workable in that reaction. Finally, 3-arylglutaconic acid anhydrides were identified as displaying the right reactivity towards a wide range of oximes (including those which did not react with homophthalic anhydride, such as derivatives of aliphatic aldehydes or ketones and substrates with nucleophilic side groups) and delivering, after 18 h at 110 °C in DMSO, β,γ-unsaturated N-hydroxylactam products lacking the carboxylic acid functionality as the result of decarboxylation accompanying the cyclocondensation process. The reaction was found to be scalable to gram quantities of the starting anhydrides. The products were shown to be easily amenable to post-condensational double-bond transposition or reduction. As expected from cyclic hydroxamic acids, the reaction products were shown to bind Fe(iii) and Cu(ii) ions (selectively out of a panel of 16 metal cations) and potentially serve as fluorescent metal sensors.

KW - Anhydrides/chemistry

KW - Ferric Compounds/chemistry

KW - Hydroxamic Acids/chemistry

KW - Indicators and Reagents

KW - Oximes/chemistry

UR - http://www.scopus.com/inward/record.url?scp=85141467729&partnerID=8YFLogxK

UR - https://www.mendeley.com/catalogue/1d2830dd-dc5c-3beb-a018-6fb6731c50ab/

U2 - 10.1039/d2ob01675c

DO - 10.1039/d2ob01675c

M3 - Article

C2 - 36281787

VL - 86

SP - 8643

EP - 8648

JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

SN - 1477-0520

IS - 44

ER -

ID: 100702384