One-step route to tricyclic fused 1,2,3,4-tetrahydro-isoquinoline systems via the castagnoli–cushman protocol

9Citations
Citations of this article
8Readers
Mendeley users who have this article in their library.

Abstract

The Castagnoli–Cushman reaction of 3,4-dihydroisoquinolines with glutaric anhydride, its oxygen and sulfur analogues was investigated as a one-step approach to the benzo[a]quinolizidine system and its heterocyclic analogs. An extension towards the pyrrolo[2,1-a]isoquinoline system was achieved with the use of succinic anhydride. The results are evidence of an unexplored method for the access of the aforementioned tricyclic annelated systems incorporating a bridgehead nitrogen atom. The structures and relative configurations of the new compounds were established by means of 1D and 2D NMR techniques. The reactions between 1-methyldihydroisoquinoline and glutaric, diglycolic and succinic anhydrides yielded unexpected isoquinoline derivatives containing an exocyclic double bond. The compounds prepared bear the potential to become building blocks for future synthetic bioactive molecules.

Cite

CITATION STYLE

APA

Pashev, A., Burdzhiev, N., & Stanoeva, E. (2020). One-step route to tricyclic fused 1,2,3,4-tetrahydro-isoquinoline systems via the castagnoli–cushman protocol. Beilstein Journal of Organic Chemistry, 16, 1456–1464. https://doi.org/10.3762/bjoc.16.121

Register to see more suggestions

Mendeley helps you to discover research relevant for your work.

Already have an account?

Save time finding and organizing research with Mendeley

Sign up for free