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Intramolecular cycloaddition of 5-alkenyl-1-pyrroline 1-oxide-5-carboxylic esters

โœ Scribed by David StC. Black; Donald C. Craig; Gavin L. Edwards; Sean M. Laaman

Publisher
Elsevier Science
Year
1998
Tongue
French
Weight
219 KB
Volume
39
Category
Article
ISSN
0040-4039

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โœฆ Synopsis

Some 5-alkenyl-1-pyrroline-1-oxide-5-carboxylic esters have been prepared by alkylation of a related nitrone carboxylic ester. On thermal treatment, they undergo regioselective intramolecular 1,3-dipolar cycloaddition to give a range of cycloadducts, which can be hydrogenolysed to generate azabicyclic compounds and unusual cyclic amino esters.

๐Ÿ“œ SIMILAR VOLUMES

ChemInform Abstract: Intramolecular Cycl
ChemInform Abstract: Intramolecular Cycloaddition of 5-Alkenyl-1-pyrroline 1-Oxide-5-carboxylic Esters.
โœ D. STC. BLACK; D. C. CRAIG; G. L. EDWARDS; S. M. LAAMAN ๐Ÿ“‚ Article ๐Ÿ“… 2010 ๐Ÿ› John Wiley and Sons โš– 32 KB ๐Ÿ‘ 2 views

Intramolecular Cycloaddition of 5-Alkenyl-1-pyrroline 1-Oxide-5carboxylic Esters. -Thermal treatment of the pyrroline-1-oxides (Ia)-(Ic) results in intramolecular cyclization to give the azatricyclo compounds (II) and (III), while (Id) fails to react. The products are subjected to hydrogenolysis, f

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โœ David StC. Black; Gavin L. Edwards; Richard H. Evans; Paul A. Keller; Sean M. La ๐Ÿ“‚ Article ๐Ÿ“… 2000 ๐Ÿ› Elsevier Science ๐ŸŒ French โš– 151 KB

Some C5 mono-and diester-substituted 1-pyrroline-1-oxides have been prepared via reductive cyclisation of the corresponding g-nitro carbonyl compounds. Ethyl 2-phenyl-1-pyrroline-1-oxide-5-carboxylate 5c was regioselectively alkylated at C5. Acylation of this molecule occurs exclusively on the nitro