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Paper | Special issue | Vol 97, No. 2, 2018, pp.755-775
Published online, 2nd April, 2018
DOI: 10.3987/COM-18-S(T)47
Synthesis of Iodinated Thiazolo[2,3-a]isoquinolinium Salts and Their Crystal Structures with/without Halogen Bond

Shoji Matsumoto,* Ryuta Sumida, Sia Er Tan, and Motohiro Akazome

*Department of Applied Chemistry and Biotechnology, Graduate School and Faculty of Engineering, Chiba University, 1-33 Yayoi-cho, Inage-ku, Chiba 263-8522, Japan

Abstract

We investigated the cyclization reaction of 2-(2-(phenylethynyl)- phenyl)thiazoles with I2. A six-membered ring was formed to produce the corresponding thiazolo[2,3-a]isoquinolin-7-ium salts. The counter anions (I and I3) varied based on the structure of the thiazole moiety. We also revealed the single-crystal X-ray structures of those thiazolo[2,3-a]isoquinolin-7- ium salts. We discovered that various structures with and without halogen bonds existed, although they were the prospective structures to make “charge-assisted halogen bonds”.