Synthesis of New C2-Symmetric Chiral Benzimidazole Derivatives Having Norbornene/Dibenzobarrelene Skeletons

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ÇAPAN İ., SERVİ S.

LETTERS IN ORGANIC CHEMISTRY, vol.17, no.10, pp.801-805, 2020 (SCI-Expanded)

• Publication Type: Article / Article
• Volume: 17 Issue: 10
• Publication Date: 2020
• Doi Number: 10.2174/1570178616666190731105327
• Journal Name: LETTERS IN ORGANIC CHEMISTRY
• Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
• Page Numbers: pp.801-805
• Keywords: Norbornene, dibenzobarrelene, guanidine, benzimidazole, chiral resolution, RESOLUTION, ACID
• Gazi University Affiliated: Yes

Abstract

Racemic dicarboxylic acids were synthesized from the Diels-Alder cycloaddition reactions which formed the dibenzobarrelene and norbomene skeletons. The pure enantiomers of these compounds were obtained using brucine as the chiral auxiliary. Novel C-2-symmetric chiral benzimidazole derivatives were synthesized from the reaction of the diaminobenzene and enantiomeric dicarboxylic acids in the presence of boric acid.