Synthesis of ortho‐Phenylenebis(guanidine) Derivatives with Potential Chirality |
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| Authors: | Masahiro Fukuzumi Waka Nakanishi Tsutomu Ishikawa Takuya Kumamoto |
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| Institution: | 1. Graduate School of Pharmaceutical Sciences, Chiba University, 1‐8‐1 Inohana, Chuo‐ku, Chiba 260‐8675, Japan (phone/fax: +81‐43‐2262944);2. Present address: Faculty of Pharmaceutical Sciences, Musashino University, 1‐1‐20 Shinmachi, Nishitokyo, Tokyo 202‐8585, Japan (phone/fax: +81‐42‐4689278). |
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| Abstract: | We report the synthesis and potential chirality of ortho‐phenylenebisguanidines (BGs) with substituents at C(3) and C(6). Guanidinylation of 3,6‐disubstituted benzene‐1,2‐diamines with 2‐chloro‐4,5‐dihydro‐1,3‐dimethyl‐1H‐imidazolium chloride gave the corresponding BGs. X‐Ray crystallography showed that the two guanidine moieties occupy different faces of the benzene ring, creating potential chirality, although optical resolution of tBu‐substituted BG by chiral HPLC failed. However, a methylated acyclic bisguanidinium salt (BGms) was obtained as a chiral crystal with a space group of P212121. |
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| Keywords: | Bis(guanidines) Benzene‐1 2‐diamines Potential chirality X‐Ray crystallography Chiral crystals |
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