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N-Alkylation and Aminohydroxylation of 2-Azidobenzenesulfonamide gives a Pyrrolobenzothiadiazepine precursor whereas attempted N-Alkylation of 2-Azidobenzamide gives Benzotriazinones and Quinazolinones

Hamasharif, Muslih S., Smith, Oliver, Curran, Collette and Hemming, Karl (2017) N-Alkylation and Aminohydroxylation of 2-Azidobenzenesulfonamide gives a Pyrrolobenzothiadiazepine precursor whereas attempted N-Alkylation of 2-Azidobenzamide gives Benzotriazinones and Quinazolinones. ACS Omega, 2 (3). pp. 1222-1231. ISSN 2470-1343

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Abstract

N-Alkylation of 2-azidobenzenesulfonamide with 5-bromopent-1-ene gave an N-pentenyl sulfonamide which underwent intramolecular aminohydroxylation to give an N-(2-azidoaryl)sulfonyl prolinol, a precursor for the synthesis of a pyrrolobenzothiadiazepine. The attempted N-alkylation of 2-azidobenzamide gave a separable mixture (~1:1) of a benzotriazinone and a quinazolinone in 72% combined yield. Other primary alkyl halides (3 examples) gave similar mixtures of benzotriazinones and quinazolinones. Benzylic, allylic, secondary and tertiary alkyl halides (5 examples) gave only the benzotriazinones in moderate yields. The results of mechanistic studies show the likely involvement of nitrene intermediates in the quinazolinone pathway and a second pathway involving a DMSO or dimethylsulfide mediated conversion of 2-azidobenzamide into the benzotriazinones.

Item Type: Article
Contributors:
ContributionNameEmailORCID
AuthorHemming, Karlk.hemming@hud.ac.ukUNSPECIFIED
UNSPECIFIEDHamasharif, Muslih S.UNSPECIFIEDUNSPECIFIED
UNSPECIFIEDSmith, OliverUNSPECIFIEDUNSPECIFIED
UNSPECIFIEDCurran, ColletteUNSPECIFIEDUNSPECIFIED
Subjects: Q Science > QD Chemistry
Schools: School of Applied Sciences
School of Applied Sciences > Biomolecular Sciences Research Centre
Related URLs:
Depositing User: Karl Hemming
Date Deposited: 20 Apr 2017 08:09
Last Modified: 20 Apr 2017 18:28
URI: http://eprints.hud.ac.uk/id/eprint/31706

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