TY - JOUR
T1 - Iodine-DMSO mediated conversion of Narylcyanothioformamides to Narylcyanoformamides and the unexpected formation of 2-cyanobenzothiazoles
AU - Moussa, Ziad
AU - Judeh, Zaher M.A.
AU - Alzamly, Ahmed
AU - Ahmed, Saleh A.
AU - Al-Masri, Harbi Tomah
AU - Al-Hindawi, Bassam
AU - Rasool, Faisal
AU - Saada, Sara
N1 - Publisher Copyright:
© 2022 Royal Society of Chemistry. All rights reserved.
PY - 2022
Y1 - 2022
N2 - 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.
AB - 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.
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U2 - 10.1039/d2ra00049k
DO - 10.1039/d2ra00049k
M3 - Article
AN - SCOPUS:85126924110
SN - 2046-2069
VL - 12
SP - 6133
EP - 6148
JO - RSC Advances
JF - RSC Advances
IS - 10
ER -