Detosylation of 3-amino-1-tosylindole-2-carbonitriles using DBU and thiophenol

Michaelidou, Sophia S.; Koutentis, Panayiotis Andreas

doi:10.1016/j.tet.2010.02.058

dc.contributor.author	Michaelidou, Sophia S.	en
dc.contributor.author	Koutentis, Panayiotis Andreas	en
dc.creator	Michaelidou, Sophia S.	en
dc.creator	Koutentis, Panayiotis Andreas	en
dc.date.accessioned	2019-11-21T06:21:27Z
dc.date.available	2019-11-21T06:21:27Z
dc.date.issued	2010
dc.identifier.uri	http://gnosis.library.ucy.ac.cy/handle/7/55849
dc.description.abstract	Attempted detosylation of the 3-amino-1-(p-tosylamino)indole-2-carbonitriles 4a-c using either K2CO3 in EtOH or DBU in PhH at reflux gives unexpectedly the 3-(N-p-tosylamino)indole-2-carbonitriles 5a-c, respectively in high yields. Nevertheless, treatment of 1-(p-tosylamino)indoles 4a-c with thiophenol and DBU in PhH at reflux gives the detosylated 3-aminoindole-2-carbonitriles 5a-c. Reaction mechanisms supporting the tosyl migration (4→5) and the reductive detosylation (4→2) are proposed. All new compounds are fully characterised. © 2010 Elsevier Ltd. All rights reserved.	en
dc.source	Tetrahedron	en
dc.source.uri	https://www.scopus.com/inward/record.uri?eid=2-s2.0-77949568856&doi=10.1016%2fj.tet.2010.02.058&partnerID=40&md5=6fd60391d778083e5c4ae9b66329bfad
dc.subject	article	en
dc.subject	migration	en
dc.subject	priority journal	en
dc.subject	unclassified drug	en
dc.subject	synthesis	en
dc.subject	chemical reaction	en
dc.subject	indole derivative	en
dc.subject	cyclization	en
dc.subject	thiophenol	en
dc.subject	3 aminoindole 2 carbonitrile	en
dc.subject	3 (n 4 tosylamino)indole 2 carbonitrile	en
dc.subject	3 amino 1 tosylindole 2 carbonitrile	en
dc.subject	detosylation	en
dc.title	Detosylation of 3-amino-1-tosylindole-2-carbonitriles using DBU and thiophenol	en
dc.type	info:eu-repo/semantics/article
dc.identifier.doi	10.1016/j.tet.2010.02.058
dc.description.volume	66
dc.description.issue	16
dc.description.startingpage	3016
dc.description.endingpage	3023
dc.author.faculty	002 Σχολή Θετικών και Εφαρμοσμένων Επιστημών / Faculty of Pure and Applied Sciences
dc.author.department	Τμήμα Χημείας / Department of Chemistry
dc.type.uhtype	Article	en
dc.description.notes	<p>Cited By :7</p>	en
dc.source.abbreviation	Tetrahedron	en
dc.contributor.orcid	Koutentis, Panayiotis Andreas [0000-0002-4652-7567]
dc.gnosis.orcid	0000-0002-4652-7567

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