1352479-70-9Relevant academic research and scientific papers
Approaches to 3,4,5-substituted piperidines via 1,2,5,6-tetrahydropyridines prepared by ring-closing metathesis
Buffat, Maxime G.P.,Thomas, Eric J.
, p. 451 - 463 (2016/01/09)
Synthetic approaches to (1RS,2SR,6SR)-7-arylmethyl-2-alkoxymethyl-4,7-diaza-9-oxabicyclo[4.3.0]nonan-8-ones, potentially selective muscarinic M1 receptor agonists, by hydration of 1,2,5,6-tetrahydropyridines were investigated. 3-Substituted N-tosyl-1,2,5,6-tetrahydropyridines were prepared by ring-closing metathesis (RCM). The direct hydration of these by hydroboration-oxidation was not usefully selective, but cis-3-hydroxymethyl-4-tert-butyldimethylsilyloxy-N-tosylpiperidine was prepared from 3-hydroxymethyl-N-tosyl-1,2,5,6-tetrahydropyridine by epoxidation, mesylation, reductive elimination, silylation and hydroboration-oxidation. Problems were encountered during attempts to prepare 3-alkoxymethyl-1,2,5,6-tetrahydropyridines with protected amino and cyclobutyl substituents at C5 by ring-closing metathesis, perhaps because of steric hindrance. Nevertheless interesting chemistry was encountered during the synthesis of the RCM precursors including a novel coupling via a 2-ethenyl-N-nosylaziridine and the formation of an oxaazathiocin by an intramolecular substitution of the nitro group of an N-nosyl protected amine by a proximate hydroxyl substituent.
A tandem 1,3-H-shift-6π-electrocyclization-cyclic 2-amido-diene intramolecular Diels-Alder cycloaddition approach to BCD-ring of atropurpuran
Hayashi, Ryuji,Ma, Zhi-Xiong,Hsung, Richard P.
supporting information; experimental part, p. 252 - 255 (2012/03/08)
An approach toward the BCD-ring of atropurpuran via a sequence of allenic 1,3-H shift, 6π-electron pericyclic ring closure, and intramolecular Diels-Alder cycloaddition of cyclic 2-amidodiene is described.
