Synthesis of ortho-Phenylenebis(guanidine) Derivatives with Potential Chirality

被引：0

作者：

Fukuzumi, Masahiro ^{[1
]}

Nakanishi, Waka ^{[1
]}

Ishikawa, Tsutomu ^{[1
]}

Kumamoto, Takuya ^{[1
]}

机构：

[1] Chiba Univ, Grad Sch Pharmaceut Sci, Chuo Ku, Chiba 2608675, Japan

来源：

HELVETICA CHIMICA ACTA | 2014年 / 97卷 / 11期

关键词：

YLIDE-MEDIATED AZIRIDINATION; GUANIDINIUM YLIDES; INTERMEDIATE; BISGUANIDINOBENZENE; CRYSTALLIZATION; SUPERBASES; CONVERSION; SKELETON;

D O I：

10.1002/hlca.201400053

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

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 P2(1)2(1)2(1).

引用

页码：1453 / 1468

页数：16

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