Abstract

MANGANESE(III) ACETATE MEDIATED SYNTHESIS OF NEW ANGULAR AND LINEAR DIHYDROFUROQUINOLINONES

Highlights

  • Quinolines are one of the most abundant molecules, naturally occurring compounds and commonly used as versatile intermediates in natural products synthesis [1,2]

  • Dihydrofuroquinolines are other important compounds that are widely distributed in nature (Fig. 1) and several methods for the synthesis of these compounds are described in the literature [3,4]

  • Effect of temperature and the molar ratio of product yield were investigated, and the best results were obtained in glacial acetic acid at 80 C in 20 minutes under nitrogen atmosphere using 2:1:3 molar ratio (1: 2: Mn(OAc)3, respectively)

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Summary

Introduction

Quinolines are one of the most abundant molecules, naturally occurring compounds and commonly used as versatile intermediates in natural products synthesis [1,2]. Dihydrofuroquinolines are other important compounds that are widely distributed in nature (Fig. 1) and several methods for the synthesis of these compounds are described in the literature [3,4]. A commonly used to obtain dihydrofuroquinolines involves cyclization reactions of carbonyl compounds with alkenes or alkynes in the presence of metal salts [5,6,7]. Manganese(III) acetate was the most preferred oxidant [8,9,10] for radical cyclization reactions and naturally occurring araliopsine [11] is synthesized by this oxidant. We report the oxidative cyclization of 4-hydroxy-1-methyl-quinoline-2-one (1) with steric hindered alkene (E)-2-(1-phenylprop-1-en-2-yl)thiophene (2) by using electrochemically synthesized Mn(OAc) which afforded 2,5-dimethyl-3-phenyl-2(thiophen-2-yl)-2,3-dihydrofuro[3,2-c]quinolin-4(5H)-one (3, 39%) as an angular product and 2,9-dimethyl-3-phenyl-2-(thiophen-2-yl)-2,3-dihydrofuro[2,3-b]quinolin4(9H)-one as a linear product (4, 28%) (Fig. 2)

MATERIALS AND METHODS
Syntheses
AND DISCUSSION
CONCLUSION

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