The Identification of a Novel Highly Condensed Pentacyclic Heteroaromatic Ring System 1, 3, 5, 5b, 6, 8, 10, 10b‐Octaazacyclopenta[h, i]Aceanthrylene and its Application in the Synthesis of 5, 7‐Substituted Pyrazolo[4, 3‐d]Pyrimidines. (29th May 2014)

• Record Type: Journal Article
• Authors: Havlíček, Libor; Moravcová, Daniela; Kryštof, Vladimír; Strnad, Miroslav
• Is Part Of: Journal of heterocyclic chemistry. Volume 52:Number 3(2015)
• Page Start: 669
• Page End: 673
• Publication Date: 2014-05-29
• Subjects: Heterocyclic compounds -- Periodicals; 547.59
• DOI: 10.1002/jhet.2147
• Languages: English
• ISSNs: 0022-152X

Abstract

<abstract abstract-type="main"> <title> <x xml:space="preserve">Abstract</x> </title> <p>Pyrazolo[4, 3‐d]pyrimidines are of interest as potential kinase inhibitors. This article describes the formation of a novel highly conjugated, condensed, centrosymmetric heteroaromatic compound, <bold>4, 9‐dichloro‐2, 7‐diisopropyl‐1, 3, 5, 5b, 6, 8, 10, 10b‐octaazacyclopenta[h, i]aceanthrylene</bold> (<bold>3</bold>), during the <named-content content-type="reactionType" xlink:type="simple" xmlns:xlink="http://www.w3.org/1999/xlink">chlorination</named-content> of 5, 7‐dihydroxypyrazolo[4, 3‐<italic>d</italic>]pyrimidine (<bold>1</bold>) with phenylphosphonic dichloride. The <named-content content-type="reactionType" xlink:type="simple" xmlns:xlink="http://www.w3.org/1999/xlink">nucleophilic</named-content> attack of benzylamine on 3 afforded <bold>N‐benzyl‐5‐chloro‐3‐isopropyl‐1H‐pyrazolo[4, 3‐d]pyrimidin‐7‐amine</bold> (<bold>6</bold>), which was further substituted to yield a pyrazolo[4, 3‐<italic>d</italic>]pyrimidine analogue of roscovitine, a well‐known cyclin‐dependent kinase inhibitor.</p> </abstract>