In:
Universitas Scientiarum, Editorial Pontificia Universidad Javeriana, Vol. 16, No. 2 ( 2011-06-02), p. 160-
Abstract:
〈 p 〉 〈 strong 〉 Objectives. 〈 /strong 〉 To prepare new N-(1,2,3,4-tetrahydroquinolin-4-yl) pyrrolidin-2-one molecules and to characterize them by spectroscopic methods. 〈 strong 〉 Materials and methods. 〈 /strong 〉 All reagents were purchased from Aldrich, commercial grade. The purity of the products and the composition of the reaction mixtures were monitored by thin layer chromatography over Silufol UV 〈 sub 〉 254 〈 /sub 〉 chromatoplates (0.25 mm). Product isolation and purification were performed by column chromatography (SiO 〈 sub 〉 2 〈 /sub 〉 ), using ethyl acetate. 〈 strong 〉 Results. 〈 /strong 〉 Preparation of new N-(2-nitrophenyl-1,2,3,4-tetrahydroquinolin-4-yl) pyrrolidin-2-ones has been achieved via the one-pot synthesis, based on a BiCl 〈 sub 〉 3 〈 /sub 〉 -catalyzed imino Diels-Alder cycloaddition reaction of toluidine, N-vinylpyrrolidin-2-one and 4-nitro- or 3-nitrobenzaldehydes. The structure of the pyrrolidine derivatives was confirmed by 〈 sup 〉 1 〈 /sup 〉 H nmr and 〈 sup 〉 13 〈 /sup 〉 C nmr studies, in addition to inverse-detected 2D NMR experiments and monocrystal X-ray diffraction. 〈 strong 〉 Conclusions. 〈 /strong 〉 An efficient, economic, and fast synthetic route (multi-component imino Diels-Alder reaction) was employed in the construction of several new tetrahydroquinoline derivatives, useful and attractive rigid skeleton with well-defined stereochemistry. 〈 /p 〉 〈 p 〉 〈 /p 〉 〈 p 〉 〈 strong 〉 Key words: 〈 /strong 〉 tetrahydroquinoline derivatives, N-substituted pyrrolidin-2-ones, three component imino Diels-Alder reaction, one-pot synthesis. 〈 /p 〉
Type of Medium:
Online Resource
ISSN:
2027-1352
,
0122-7483
DOI:
10.11144/javeriana.SC16-2.spon
Language:
Unknown
Publisher:
Editorial Pontificia Universidad Javeriana
Publication Date:
2011
detail.hit.zdb_id:
2233913-9
SSG:
7,36
Permalink