Affiliation:
1. Department of Chemistry, Faculty of Science, The University of Jordan, Amman, 11942, Jordan | Pharmacological and Diagnostic Research Center, Faculty of Pharmacy, Al-Ahliyya Amman University, Amman 19328, Jordan
2. Department of Chemistry, Faculty of Science, The University of Jordan, Amman, 11942, Jordan
Abstract
Background:
A direct synthesis of functionalized spiro[oxindole-3,3'-pyrrolines] is
achieved via thermodynamic control (~60 oC), three-component 1,4-dipolar cycloaddition
reaction involving 3-phenylimidazo[5,1-a]isoquinoline, dimethyl acetylenedicarboxylate, and
N-alkylisatins.
Methods:
Conversely, this one-pot reaction furnished, upon conduction at 25–38 oC, the expected
1,3-oxazepino[7,6-b]indoles as the main kinetic control products. The calculated energy
of the optimized molecular structures of model spiro-oxindole and its isomeric oxazepinoindole
indicate that spiro-oxindole is more stable by 76.1 kJ/mol.
Results:
The structures of the synthesized spiro adducts were evidenced from NMR and MS
spectral data and further confirmed by single-crystal X-ray diffraction. Characteristic features
of the spiro-oxindoles are displaced in their 13C-spectra as diagnostic signals at ~53 and ~70 ppm assigned, respectively,
to the spiro carbon-3 and sp3 CH-2' of the pyrroline ring.
Conclusion:
This unprecedented thermally induced pathway in 1,4-dipolar cycloaddition, utilizing imidazo[5,1-
a]isoquinoline and related congeners, would serve as a new route towards the synthesis of spiro[oxindole-3,3'-
pyrrolines], a class of diverse biological activities. An insight into the thermodynamic control pathway is presented.
Publisher
Bentham Science Publishers Ltd.
Cited by
3 articles.
订阅此论文施引文献
订阅此论文施引文献,注册后可以免费订阅5篇论文的施引文献,订阅后可以查看论文全部施引文献