An Efficient Synthesis of Bibenzylic Oxygen Heterocycles

Kumbhar, Virendra B.; Joseph, Augustine R.; Natu, Arun D.; Kusurkar, Radhika S.; Paradkar, M. V.

doi:10.3184/030823407x256091

Cited by 5 publications

(2 citation statements)

References 5 publications

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“…(9): Light brown oil (lit. 30 Reduction of deoxybenzoins; general procedure Deoxybenzoins 9-11 (2 mmol) were dissolved in distilled methanol (75 mL) under stirring. To this solution was added sodium borohydride (10 mmol) in portions, under stirring.…”

Section: Synthesis Of Deoxybenzoin Intermediates; General Proceduresmentioning

confidence: 99%

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Convenient Syntheses of 3-Aryl-3,4-Dihydroisocoumarins

Limaye

Joseph

Natu

et al. 2015

Journal of Chemical Research

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A convenient method for the synthesis of naturally occurring 3,4-dihydroisocoumarins by judicious use of Friedel-Craft acylation, regioselective formylation and oxidative cyclisation reactions is described. O-methylated analogues of montroumarin and thunberginols C and D and have been synthesised using 3,5-dimethoxyphenylacetic acid as a starting material. Furthermore, the starting material 3,5-dimethoxyphenylacetic acid was synthesised by a route involving an oxidative Nef reaction.

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Section: Synthesis Of Deoxybenzoin Intermediates; General Proceduresmentioning

confidence: 99%

“…It was characterised by using spectroscopic techniques and confirmed as 9 by comparison with literature data. 30 The deoxybenzoin 9 thus obtained was then subjected to reduction using sodium borohydride in methanol at room temperature. The reaction was over in 1 h and it was decomposed using icecold solution of NH 4 Cl.…”

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confidence: 99%

Convenient Syntheses of 3-Aryl-3,4-Dihydroisocoumarins

Limaye

Joseph

Natu

et al. 2015

Journal of Chemical Research

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ChemInform Abstract: An Efficient Synthesis of Bibenzylic Oxygen Heterocycles.

et al. 2008

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Applications of the Wittig Reaction on the Synthesis of Natural and Natural‐Analogue Heterocyclic Compounds

2018

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More than sixty years after its discovery, the Wittig reaction still is a powerful tool to create carbon–carbon double bonds. The large diversity of high‐yielding and stereoselective reactions that can be achieved, even for highly functionalized molecules, is presented, demonstrating that the Wittig reaction is an efficient and attractive strategy in synthetic organic chemistry. The principles of the reaction will be briefly presented and discussed, but the focus will be on the most recent reports using this reaction in the synthesis of heterocyclic compounds. A comprehensive discussion on its application in the total synthesis of natural products and in the synthesis of natural analogues will be presented. Emphasis will be given to important organic molecules that present interesting biological activities. The purpose of this short review is to highlight the advances in this general area by presenting such newer applications in organic synthesis and eventually guide future researchers.

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An Efficient Synthesis of Bibenzylic Oxygen Heterocycles

Abstract: The first total syntheses of naturally occurring 6-methoxy-4-(2-phenylethyl)benzofuran (1) and 2,2-dimethyl-7methoxy-5-(2-phenylethyl)chroman (2) and the non-natural 7-methoxy-5-(2-phenylethyl)chromen-2-one (3) are described from 3,5-dimethoxyphenylacetic acid in good yields.

Cited by 5 publications

References 5 publications

Convenient Syntheses of 3-Aryl-3,4-Dihydroisocoumarins

Convenient Syntheses of 3-Aryl-3,4-Dihydroisocoumarins

ChemInform Abstract: An Efficient Synthesis of Bibenzylic Oxygen Heterocycles.

Applications of the Wittig Reaction on the Synthesis of Natural and Natural‐Analogue Heterocyclic Compounds

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