Alkylation of oxazolones and related heterocycles through an SN1 reaction

Andrea Nekane R. Alba; Teresa Calbet; Mercé Font-Bardía; Albert Moyano; Ramon Rios

doi:10.1002/ejoc.201100046

Alkylation of oxazolones and related heterocycles through an S_N1 reaction

Andrea Nekane R. Alba, Teresa Calbet, Mercé Font-Bardía, Albert Moyano, Ramon Rios

Chemistry

Universitat de Barcelona

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

16 Scopus citations

Abstract

The alkylation of oxazolones through an S_N1 reaction by using stabilized carbocations is reported. The reaction (catalyzed by Brønsted acids, such as TFA or thioureas) affords the final compounds in excellent yields. Reaction with other heterocycles has also been studied, rendering pyrazolone or oxindole derivatives in good yields.

Original language	British English
Pages (from-to)	2053-2056
Number of pages	4
Journal	European Journal of Organic Chemistry
Issue number	11
DOIs	https://doi.org/10.1002/ejoc.201100046
State	Published - Apr 2011

Keywords

Alcohols
Brønsted acids
Green chemistry
Lewis acids
Nucleophilic substitution

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10.1002/ejoc.201100046

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title = "Alkylation of oxazolones and related heterocycles through an SN1 reaction",

abstract = "The alkylation of oxazolones through an SN1 reaction by using stabilized carbocations is reported. The reaction (catalyzed by Br{\o}nsted acids, such as TFA or thioureas) affords the final compounds in excellent yields. Reaction with other heterocycles has also been studied, rendering pyrazolone or oxindole derivatives in good yields.",

keywords = "Alcohols, Br{\o}nsted acids, Green chemistry, Lewis acids, Nucleophilic substitution",

author = "Alba, \{Andrea Nekane R.\} and Teresa Calbet and Merc{\'e} Font-Bard{\'i}a and Albert Moyano and Ramon Rios",

year = "2011",

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doi = "10.1002/ejoc.201100046",

language = "British English",

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journal = "European Journal of Organic Chemistry",

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AU - Alba, Andrea Nekane R.

AU - Calbet, Teresa

AU - Font-Bardía, Mercé

AU - Moyano, Albert

AU - Rios, Ramon

PY - 2011/4

Y1 - 2011/4

N2 - The alkylation of oxazolones through an SN1 reaction by using stabilized carbocations is reported. The reaction (catalyzed by Brønsted acids, such as TFA or thioureas) affords the final compounds in excellent yields. Reaction with other heterocycles has also been studied, rendering pyrazolone or oxindole derivatives in good yields.

AB - The alkylation of oxazolones through an SN1 reaction by using stabilized carbocations is reported. The reaction (catalyzed by Brønsted acids, such as TFA or thioureas) affords the final compounds in excellent yields. Reaction with other heterocycles has also been studied, rendering pyrazolone or oxindole derivatives in good yields.

KW - Alcohols

KW - Brønsted acids

KW - Green chemistry

KW - Lewis acids

KW - Nucleophilic substitution

UR - https://www.scopus.com/pages/publications/79953250248

U2 - 10.1002/ejoc.201100046

DO - 10.1002/ejoc.201100046

M3 - Article

AN - SCOPUS:79953250248

SN - 1434-193X

SP - 2053

EP - 2056

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

IS - 11

ER -

Alkylation of oxazolones and related heterocycles through an S_N1 reaction

Abstract

Keywords

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