Rearrangement of o-(pivaloylaminomethyl)benzaldehydes: an experimental and computational study

Treatment of alkoxy-substituted o-(pivaloylaminomethyl)benzaldehydes under acidic conditions resulted in the formation of the regioisomeric aldehydes and/or dimer-like products. Detailed NMR studies and single-crystal X-ray measurements supported the structure elucidation of the compounds. DFT calcu...

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Main Authors:	Csilla Hargitai, Györgyi Koványi-Lax, Tamás Nagy, Péter Ábrányi-Balogh, András Dancsó, Gábor Tóth, Judit Halász, Angéla Pandur, Gyula Simig, Balázs Volk
Format:	Article
Language:	English
Published:	Beilstein-Institut 2020-07-01
Series:	Beilstein Journal of Organic Chemistry
Subjects:	dft calculations nmr reaction mechanism rearrangement ring-chain tautomerism
Online Access:	https://doi.org/10.3762/bjoc.16.136

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spelling	doaj-4519f43ebccc4132b2066bfbe53f84d22021-04-02T12:47:35ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972020-07-011611636164810.3762/bjoc.16.1361860-5397-16-136Rearrangement of o-(pivaloylaminomethyl)benzaldehydes: an experimental and computational studyCsilla Hargitai0Györgyi Koványi-Lax1Tamás Nagy2Péter Ábrányi-Balogh3András Dancsó4Gábor Tóth5Judit Halász6Angéla Pandur7Gyula Simig8Balázs Volk9Directorate of Drug Substance Development, Egis Pharmaceuticals Plc., P.O. Box 100, H-1475 Budapest, HungaryDirectorate of Drug Substance Development, Egis Pharmaceuticals Plc., P.O. Box 100, H-1475 Budapest, HungaryDirectorate of Drug Substance Development, Egis Pharmaceuticals Plc., P.O. Box 100, H-1475 Budapest, HungaryMedicinal Chemistry Research Group, Research Centre for Natural Sciences, P.O. Box 286, H-1519 Budapest, HungaryDirectorate of Drug Substance Development, Egis Pharmaceuticals Plc., P.O. Box 100, H-1475 Budapest, HungaryDirectorate of Drug Substance Development, Egis Pharmaceuticals Plc., P.O. Box 100, H-1475 Budapest, HungaryDirectorate of Drug Substance Development, Egis Pharmaceuticals Plc., P.O. Box 100, H-1475 Budapest, HungaryDirectorate of Drug Substance Development, Egis Pharmaceuticals Plc., P.O. Box 100, H-1475 Budapest, HungaryDirectorate of Drug Substance Development, Egis Pharmaceuticals Plc., P.O. Box 100, H-1475 Budapest, HungaryDirectorate of Drug Substance Development, Egis Pharmaceuticals Plc., P.O. Box 100, H-1475 Budapest, HungaryTreatment of alkoxy-substituted o-(pivaloylaminomethyl)benzaldehydes under acidic conditions resulted in the formation of the regioisomeric aldehydes and/or dimer-like products. Detailed NMR studies and single-crystal X-ray measurements supported the structure elucidation of the compounds. DFT calculations were also carried out to clarify the reaction mechanism, and to explain the observed product distributions and structural variances in the dimer-like products. Studies on the transformation of unsubstituted o-(pivaloylaminomethyl)benzaldehyde under similar conditions were presented as well.https://doi.org/10.3762/bjoc.16.136dft calculationsnmrreaction mechanismrearrangementring-chain tautomerism
collection	DOAJ
language	English
format	Article
sources	DOAJ
author	Csilla Hargitai Györgyi Koványi-Lax Tamás Nagy Péter Ábrányi-Balogh András Dancsó Gábor Tóth Judit Halász Angéla Pandur Gyula Simig Balázs Volk
spellingShingle	Csilla Hargitai Györgyi Koványi-Lax Tamás Nagy Péter Ábrányi-Balogh András Dancsó Gábor Tóth Judit Halász Angéla Pandur Gyula Simig Balázs Volk Rearrangement of o-(pivaloylaminomethyl)benzaldehydes: an experimental and computational study Beilstein Journal of Organic Chemistry dft calculations nmr reaction mechanism rearrangement ring-chain tautomerism
author_facet	Csilla Hargitai Györgyi Koványi-Lax Tamás Nagy Péter Ábrányi-Balogh András Dancsó Gábor Tóth Judit Halász Angéla Pandur Gyula Simig Balázs Volk
author_sort	Csilla Hargitai
title	Rearrangement of o-(pivaloylaminomethyl)benzaldehydes: an experimental and computational study
title_short	Rearrangement of o-(pivaloylaminomethyl)benzaldehydes: an experimental and computational study
title_full	Rearrangement of o-(pivaloylaminomethyl)benzaldehydes: an experimental and computational study
title_fullStr	Rearrangement of o-(pivaloylaminomethyl)benzaldehydes: an experimental and computational study
title_full_unstemmed	Rearrangement of o-(pivaloylaminomethyl)benzaldehydes: an experimental and computational study
title_sort	rearrangement of o-(pivaloylaminomethyl)benzaldehydes: an experimental and computational study
publisher	Beilstein-Institut
series	Beilstein Journal of Organic Chemistry
issn	1860-5397
publishDate	2020-07-01
description	Treatment of alkoxy-substituted o-(pivaloylaminomethyl)benzaldehydes under acidic conditions resulted in the formation of the regioisomeric aldehydes and/or dimer-like products. Detailed NMR studies and single-crystal X-ray measurements supported the structure elucidation of the compounds. DFT calculations were also carried out to clarify the reaction mechanism, and to explain the observed product distributions and structural variances in the dimer-like products. Studies on the transformation of unsubstituted o-(pivaloylaminomethyl)benzaldehyde under similar conditions were presented as well.
topic	dft calculations nmr reaction mechanism rearrangement ring-chain tautomerism
url	https://doi.org/10.3762/bjoc.16.136
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Rearrangement of o-(pivaloylaminomethyl)benzaldehydes: an experimental and computational study

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