15313-45-8Relevant articles and documents
Iodine-DMSO mediated conversion of Narylcyanothioformamides to Narylcyanoformamides and the unexpected formation of 2-cyanobenzothiazoles
Ahmed, Saleh A.,Al-Hindawi, Bassam,Al-Masri, Harbi Tomah,Alzamly, Ahmed,Judeh, Zaher M. A.,Moussa, Ziad,Rasool, Faisal,Saada, Sara
, p. 6133 - 6148 (2022/03/31)
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.
POCl3-mediated reaction of 1-Acyl-1-carbamoyl Oximes: A new entry to cyanoformamides
Yang, Jiming,Xiang, Dexuan,Zhang, Rui,Zhang, Ning,Liang, Yongjiu,Dong, Dewen
supporting information, p. 809 - 811 (2015/03/18)
A facile and efficient one-pot synthesis of cyanoformamides was developed from readily available 1-acyl-1-carbamoyl oximes mediated by phosphoryltrichloride (POCl3) under mild conditions in good to high yields.
