One-pot tandem Ugi-4CR/S(N)Ar approach to highly functionalized quino[2,3-b][1,5]benzoxazepines

Mehdi Ghandi; Nahid Zarezadeh; Alireza Abbasi

doi:10.1007/s11030-015-9651-x

One-pot tandem Ugi-4CR/S(N)Ar approach to highly functionalized quino[2,3-b][1,5]benzoxazepines

Mol Divers. 2016 May;20(2):483-95. doi: 10.1007/s11030-015-9651-x. Epub 2015 Dec 24.

Authors

Mehdi Ghandi¹, Nahid Zarezadeh², Alireza Abbasi²

Affiliations

¹ School of Chemistry, College of Science, University of Tehran, P.O. Box 14155 6455, Tehran, Iran. ghandi@khayam.ut.ac.ir.
² School of Chemistry, College of Science, University of Tehran, P.O. Box 14155 6455, Tehran, Iran.

PMID: 26703123
DOI: 10.1007/s11030-015-9651-x

Abstract

We have developed a convenient and facile method for the synthesis of functionalized diverse quino[2,3-b][1,5]benzoxazepines. These new compounds were synthesized through a one-pot sequential Ugi-4CR/base-free intramolecular aromatic nucleophilic substitution (S(N)Ar) reaction in moderate to good yields from readily available starting materials. Structural confirmation of the products is confirmed by analytical data and X-ray crystallography.

Keywords: 2-Chloroquinoline-3-carbaldehyde; MCRs; Quino[2, 3-b][1, 5]benzoxazepine; Ugi reaction; reaction.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Benzoxazines / chemical synthesis*
Benzoxazines / chemistry*
Chemistry Techniques, Synthetic
Quinones / chemistry*

Substances

Benzoxazines
Quinones