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Cyanoacetylation of indoles, pyrroles and aromatic amines with the combination cyanoacetic acid and acetic anhydride
Unit for Organic Chemistry, Department of Biosciences, Karolinska Institute and Södertörn University College, Novum Research Park,.ORCID iD: 0000-0002-8444-181X
Unit for Organic Chemistry, Department of Biosciences, Karolinska Institute and Södertörn University College, Novum Research Park,.
Unit for Organic Chemistry, Department of Biosciences, Karolinska Institute and Södertörn University College, Novum Research Park,.
2004 (English)In: Synthesis (Stuttgart), ISSN 0039-7881, E-ISSN 1437-210X, no 16, 2760-2765 p.Article in journal (Refereed) Published
Abstract [en]

Cyanoacetic acid was activated with acetic anhydride and when heated this reagent reacted with a variety of both activated and deactivated pyrroles, indoles and aniline derivs. For example, the cyanoacetylation of 1H-indole using acetic anhydride/cyanoacetic acid gave β-oxo-1H-indole-3-propanenitrile. The same reaction using 6-amino-1,3-dimethyl-2,4(1H,3H)-pyrimidinedione (I) gave 6-amino-1,2,3,4-tetrahydro-1,3-dimethyl-β,2,4-trioxo-5-pyrimidinepropanenitrile (II).

Place, publisher, year, edition, pages
2004. no 16, 2760-2765 p.
Keyword [en]
cyanoacetylation indole pyrrole arom amine cyanoacetic acid acetic anhydride, acylation arom electrophilic substitution indole pyrrole, pyrrole propanenitrile oxo cyanoacetylation acetic anhydride cyanoacetic acid, indole propanenitrile oxo cyanoacetylation acetic anhydride cyanoacetic acid, carbazole propanenitrile oxo cyanoacetylation acetic anhydride cyanoacetic acid, pyrimidine propanenitrile oxo cyanoacetylation acetic anhydride cyanoacetic acid, cyanoacetamide cyanophenyl cyanoacetylation acetic anhydride cyanoacetic acid
National Category
Organic Chemistry
Identifiers
URN: urn:nbn:se:kth:diva-92000DOI: 10.1055/s-2004-831164ISI: 000225051500029OAI: oai:DiVA.org:kth-92000DiVA: diva2:511789
Note
QC 20120327Available from: 2012-03-23 Created: 2012-03-23 Last updated: 2017-12-07Bibliographically approved

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Slätt, Johnny

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