A novel strategy for the synthesis of 6H-chromeno [4, 3-b] quinoline by intramolecular Heck cyclization

Morteza Shiri,Mina Fathollahi-Lahroud,Zahra Yasaei

doi:10.1016/j.tet.2017.03.043

Morteza Shiri, Mina Fathollahi-Lahroud + Show 1 more

Open Access

https://doi.org/10.1016/j.tet.2017.03.043

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Journal: Tetrahedron	Publication Date: Mar 18, 2017
Citations: 23	License type: elsevier-specific: oa user license

Affiliation: Alzahra University

Abstract

A novel procedure for the synthesis of various derivatives of 6H-chromeno [4, 3-b] quinolines from intramolecular Heck reaction of 2-chloro-3-(phenoxymethyl) quinolines is described in this study. Intramolecular cyclization of N-alkylated indoles was efficiently investigated as well. The reaction is catalyzed by bis (triphenylphosphine) palladium (II) dichloride in acetonitrile at 80 °C.

Highlights

An understanding of the details of C-C bond formation of organometallic reactions, has persuaded chemists to use this strong key step in pharmaceutical and total synthesis of natural products
Intramolecular Heck reaction is a straightforward approach to the synthesis of pharmaceuticals2 heterocycles and in total synthesis3, because very sterically hindered C-C bond forming in mild conditions is possible
In accordance with the importance of activation of C-X bonds by intramolecular Heck procedure, quinolines and heteroaromatic compounds contain the moiety of significant frameworks, and they are a part of biological synthetic drugs or natural products

Summary

Introduction

An understanding of the details of C-C bond formation of organometallic reactions, has persuaded chemists to use this strong key step in pharmaceutical and total synthesis of natural products. Intramolecular Heck reaction is a straightforward approach to the synthesis of pharmaceuticals heterocycles and in total synthesis, because very sterically hindered C-C bond forming in mild conditions is possible.. To the best of our knowledge, aryl chlorides are not generally very reactive reagents in Heck coupling reactions; by installing electron-accepting substitutions they become useful counterparts.. In accordance with the importance of activation of C-X bonds by intramolecular Heck procedure, quinolines and heteroaromatic compounds contain the moiety of significant frameworks, and they are a part of biological synthetic drugs or natural products.. Quinoline by the activation of C-Cl bond of 1 in an intramolecular Heck coupling (Scheme 1)

Results and discussion

Conclusions

Experimental section