Iodine-DMSO mediated conversion of Narylcyanothioformamides to Narylcyanoformamides and the unexpected formation of 2-cyanobenzothiazoles

Ziad Moussa, Zaher M.A. Judeh, Ahmed Alzamly, Saleh A. Ahmed, Harbi Tomah Al-Masri, Bassam Al-Hindawi, Faisal Rasool, Sara Saada

Research output: Contribution to journalArticlepeer-review

1 Citation (Scopus)

Abstract

Cyanoformamides are ubiquitous as useful components for assembling key intermediates and bioactive molecules. The development of an efficient and simple approach to this motif is a challenge. Herein, we demonstrate the effectiveness of the I2-DMSO oxidative system in the preparation of Narylcyanoformamides from N-arylcyanothioformamides. The synthetic method features mild conditions, broad substrate scope, and high reaction efficiency. Furthermore, this method provides an excellent entry to exclusively afford 2-cyanobenzothiazoles which are useful substrates to access new luciferin analogs. The structures of all new products were elucidated by multinuclear NMR spectroscopy and high accuracy mass spectral analysis. Crystal-structure determination by means of single-crystal X-ray diffraction was carried out on (4-bromophenyl)carbamoyl cyanide, 5,6-dimethoxybenzo[d]thiazole-2- carbonitrile, 5-(benzyloxy)benzo[d]oxazole-2-carbonitrile, 4,7-dimethoxybenzo[d]thiazole-2-carbonitrile, and (5-iodo-2,4-dimethoxyphenyl)carbamoyl cyanide, a key intermediate with mechanistic implications.

Original languageEnglish
Pages (from-to)6133-6148
Number of pages16
JournalRSC Advances
Volume12
Issue number10
DOIs
Publication statusPublished - 2022

ASJC Scopus subject areas

  • Chemistry(all)
  • Chemical Engineering(all)

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