Titanium Tetraiodide/Trimethylsilyl Iodide Synergistically Induced Cyclization of N-(2-Cyanophenyl)benzamides into 2-Aryl-4-iodoquinazolines

Iwao Hachiya; Shintaro Nagoshi; Makoto Shimizu

doi:10.1021/acsomega.9b01199

Titanium Tetraiodide/Trimethylsilyl Iodide Synergistically Induced Cyclization of N-(2-Cyanophenyl)benzamides into 2-Aryl-4-iodoquinazolines

ACS Omega. 2019 Jun 17;4(6):10463-10473. doi: 10.1021/acsomega.9b01199. eCollection 2019 Jun 30.

Authors

Iwao Hachiya¹, Shintaro Nagoshi¹, Makoto Shimizu^{1

2}

Affiliations

¹ Department of Chemistry for Materials, Graduate School of Engineering, Mie University, Tsu, Mie 514-8507, Japan.
² School of Energy Science and Engineering, Nanjing Tech University, Nanjing 211816, Jiangsu Province, China.

Abstract

Synthesis of 2-aryl-4-iodoquinazolines is developed using titanium tetraiodide/trimethylsilyl iodide synergistically induced cyclization of N-(2-cyanophenyl)benzamides. The cyclization reactions proceeded to give the 2-aryl-4-iodoquinazolines in moderate to high yields. Remarkable synergetic effect of titanium tetraiodide and trimethylsilyl iodide was observed to promote the cyclization. The method was applied to the formal synthesis of a potent analgesic agent.