An easy access to diversely fused dioxa-2-aza-tricyclo[n.3.1.02,n]tetra/pentadecanes under solvent-free condition

doi:10.1016/j.tetlet.2011.08.080

Tetrahedron Letters

Volume 52, Issue 42, 19 October 2011, Pages 5516-5520

https://doi.org/10.1016/j.tetlet.2011.08.080 Get rights and content

Abstract

Efficient syntheses of phenyl/N-heterocycle fused 6,13-dioxa-2-aza-tricyclo[8.3.1.0^2,8]tetradecanes have been accomplished from 8-hydroxy quinoline derivatives under solvent-free condition, using basic alumina as the solid support. The methodology was successfully extended for the synthesis of corresponding pentadecane derivatives under similar reaction conditions. In terms of its general applicability, product yield, reaction time and effortless separation techniques, the methodology is more valuable compared to the solution phase protocols.

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Acknowledgments

We thank the Council of Scientific and Industrial Research (CSIR), New Delhi, for financial support in the form of fellowships to R.P., S.M., A.M., K.B.S., S.N., P.S. and A.H. We are indebted to Mr. E. Padmanaban and Mr. K. Sarkar for NMR and mass spectral analysis and also to Dr B. Achari, Emeritus Scientist, CSIR, for critical suggestions and encouragement.

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An easy access to diversely fused dioxa-2-aza-tricyclo[n.3.1.02,n]tetra/pentadecanes under solvent-free condition

Abstract

Graphical abstract

Section snippets

Acknowledgments

Biochem. Biophys. Res. Commun.

Tetrahedron: Asymmetry

J. Am. Chem. Soc.

Bull. Chem. Soc. Jpn.

Tetrahedron Lett.

J. Org. Chem.

Tetrahedron

Synlett

Tetrahedron Lett.

Helv. Chim. Acta

Arkivoc

Tetrahedron Lett.

Tetrahedron

Tetrahedron

Tetrahedron Lett.

Tetrahedron Lett.

Green Chem.

J. Chem. Educ.

Beilstein J. Org. Chem.

Tetrahedron Lett.

J. Prakt. Chem.

An easy access to diversely fused dioxa-2-aza-tricyclo[n.3.1.0^2,ⁿ]tetra/pentadecanes under solvent-free condition