New Members of the Cinchona Alkaloids Family: Assembly of the Triazole Heterocycle at the 6′ Position

Molecules

Martin Heiko Franz¹  Catalin Vasile Maftei¹  Christian Kleeberg²  Ion Neda² 

[1] InnoChemTech GmbH, Hagenring 30, 38106 Braunschweig, Germany;Institut für Anorganische und Analytische Chemie, Technische Universität ‘Carola-Wilhelmina’ Braunschweig, Hagenring 30, 38106 Braunschweig, Germany;

关键词: [3 + 2] cycloaddition;    Cinchona alkaloids;    triazoles;    quincorine;    quincoridine;   

DOI  :  10.3390/molecules26113357

来源: DOAJ

【 摘 要 】

The substance class of the well-known Cinchona alkaloids is widened by 6′-Amino-cinchonine and 6′-Amino-cinchonidine, novel compounds which incorporate a primary amino function in the quinolinic ring system. These key intermediates open the field for a range of fruitful chemistry. Here is described a short and direct pathway for the synthesis of triazole containing derivatives of the above-mentioned substances using the [3 + 2] Huisgen cycloaddition. For this purpose, the amines were first converted into the corresponding azides. Based on this, non-substituted and silyl-protected triazoles were synthesized as examples. Furthermore, didehydrated derivatives of quincorine and quincoridine were used as addition partners, resulting in compounds that carry the quinuclidine ring of the cinchona alkaloids at both ends. Some of these compounds were examined radiographically to investigate the position of the quinuclidine ring to the triazole. The solid-state structures of compounds 10, 11 and 28 were determined by X-ray diffraction analyses.

【 授权许可】

Unknown