Tetrahydroquinolizinium ylides: Preparation and 1,3-dipolar cycloaddition

Citation
Ei. Kostik et al., Tetrahydroquinolizinium ylides: Preparation and 1,3-dipolar cycloaddition, J ORG CHEM, 66(5), 2001, pp. 1638-1646
Citations number
13
Language
INGLESE
art.tipo
Article
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
JOURNAL OF ORGANIC CHEMISTRY
ISSN journal
0022-3263 → ACNP
Volume
66
Issue
5
Year of publication
2001
Pages
1638 - 1646
Database
ISI
SICI code
0022-3263(20010309)66:5<1638:TYPA1C>2.0.ZU;2-K
Abstract
By the Cu(II)-catalyzed reaction of 2-(4-diazo-3-oxoalkyl)pyridines (2), 4- alkoxycarbonyl (or 4-acyl)3-oxo-1,2,3,4-tetrahydroquinolizinium ylides (3) were obtained in high yields. From the cycloaddition reaction of 3 with ace tylenic esters (propynoates or acetylenedicarboxylates) the labile [2 + 3] cycloadducts, 3-oxo-3H-2a,4,5,8a-tetrahydropyrrolo[2, 1,5-de]quinolizine-2a -carboxylates (8 or 12), were identified, which further reacted with DMAD ( dimethyl acetylenedicarboxylate) to afford azocine derivatives (15 or 16) a nd produced pyrrolodihydroquinolizines (9 or 20) by dealkoxycarbonylation.