Highly modular assembly of cationic helical scaffolds: rapid synthesis of diverse helquats via differential quaternization

Severa, L.a and Adriaenssens, L.a and Vávra, J.a and Šaman, D.a and Císa�ová, I.b and Fiedler, P.a and Teplý, F.a (2010) Highly modular assembly of cationic helical scaffolds: rapid synthesis of diverse helquats via differential quaternization. Tetrahedron, 66 (19). pp. 3537-3552. ISSN 00404020

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Item Type:Article
Item Status:Live Archive

Abstract

A protocol for rapid and highly modular assembly of a diverse set of helquats is described. From a common bis-isoquinoline precursor, two successive distinct pyridine-type nitrogen quaternizations followed by rhodium-catalyzed 2+2+2 cycloaddition afford non-symmetric 7helquats. This route allows for straightforward molecular editing of cationic helical skeletons as exemplified by the synthesis of 15 different 5-, 6-, and 7helquats. © 2010 Elsevier Ltd. All rights reserved.

Additional Information:cited By 23 The final published version of this article can be accessed online at https://www.sciencedirect.com/science/article/pii/S0040402010003613
Keywords:fused carbon nitrogen heterocycle, helquat, molecular scaffold, rhodium, unclassified drug, article, catalysis, cycloaddition, isomerization, priority journal, reaction analysis, synthesis
Subjects:F Physical Sciences > F100 Chemistry
Divisions:College of Science > School of Chemistry
ID Code:22742
Deposited On:25 Jul 2018 10:42

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