Efficient synthesis of 4-sulfanylcoumarins from 3-bromo-coumarins<i>via</i>a highly selective DABCO-mediated one-pot thia-Michael addition/elimination process

Mostardeiro, Vitor Bastianello; Dilelio, Marina C.; Kaufman, Teodoro S.; Silveira, Cláudio C.

doi:10.1039/c9ra09545d

Cited by 6 publications

(2 citation statements)

References 76 publications

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“…The oxidative halogenation of α,β‐enones/alkenes, arenes, amides/lactams/carbamates, aromatic methyl ketones, allylic/homoallylic alcohols, thiols/disulfides, and pyrazoles have been reported with the combination of oxone and metal halides (NaX/KX). There is another report by using HBr in presence of oxone in DCM solvent . Further, the cyclization of tryptamine & tryptophol also have been reported with oxone/NaX .…”

Section: Introductionmentioning

confidence: 88%

Regioselective Halogenation of 2H‐Chromenones Promoted by Oxone and NaX: A Facile Approach for the Preparation of Halochromenones and 2H‐Chromenone Natural Products

et al. 2020

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A systematic study has been conducted for the regioselective halogenation of 2H‐chromenones to prepare 3‐halo‐2H‐chromenones, 4‐substituted 3‐halo‐2H‐chromenones and 3‐(2‐haloacetyl)‐2H‐chromenones. Commercially available NaCl/NaBr has been used as halogen source and oxone as an oxidant to produce the compounds. Further, the method has been successfully applied for the preparation of pharmaceutically important halogenated 2H‐chromenone natural products. The present approach is simple, economically viable and provided the target compounds with good yields.

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Section: Introductionmentioning

confidence: 88%

Regioselective Halogenation of 2H‐Chromenones Promoted by Oxone and NaX: A Facile Approach for the Preparation of Halochromenones and 2H‐Chromenone Natural Products

et al. 2020

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“…26 In 2020, Dong et al realized the cobalt-catalyzed aroylation of primary amines, using aryl acyl peroxides as the acyl source, without additional base or oxidant, and the synthesis of amides was realized with high efficiency and high selectivity. 27 Based on the application of DABCO in organic synthesis, including domino reactions, Michael additions, reductive couplings, and cyclization reactions, [28][29][30][31] we proposed an efficient DABCO-mediated synthesis of aromatic esters from phenols, naphthols or 3-hydroxypyridines and aryl acyl peroxides at room temperature (Scheme 1d). Scheme 1.…”

Section: Introductionmentioning

confidence: 99%

DABCO-mediated synthesis of aromatic esters from phenols, naphthols or 3-hydroxypyridines and aryl acyl peroxides at room temperature

Zhu¹,

Yan²,

Li³

et al. 2022

Arkivoc

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An efficient and practical method for the synthesis of aromatic esters from aryl acyl peroxides and phenols, naphthols or 3-hydroxypyridines at room temperature was realized. A series of aromatic esters were synthesized in high yields and with excellent selectivity in the presence of 1,4-diaza[2.2.2]bicyclooctane (DABCO) without the use of transition-metals or acid catalysts. This operation is simple, and it has a good compatibility with various functional groups, especially with heterocyclic pyridine substrates.

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Decarboxylative Iodination of Coumarin‐3‐carboxylic Acids: A Facile Access to 3‐Iodocoumarins

Thotathil,

Sidiq,

Idoudi

et al. 2024

Asian J Org Chem

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A straightforward protocol for the direct conversion of readily available coumarin‐3‐carboxylic acids to the corresponding 3‐iodocoumarins is described herein. Heating acetonitrile solution of coumarin‐3‐carboxylic acids, molecular iodine and potassium hydrogen phosphate resulted in the decarboxylative iodination of coumarin‐3‐carboxylic acids via radical mechanism. Various electron rich and electron poor coumarin‐3‐carboxylic acids were compatible with the established reaction conditions and consequently afforded the corresponding 3‐iodocoumarins in (46‐93%) reaction yields with minimum purification efforts. The formed products serve as valuable precursors to streamline more complex organic compounds incorporating coumarin core.

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Efficient synthesis of 4-sulfanylcoumarins from 3-bromo-coumarinsviaa highly selective DABCO-mediated one-pot thia-Michael addition/elimination process

Abstract: A facile, simple and metal-free protocol for the 4-sulfanylation of 3-bromocoumarins was developed. It involves a thia-Michael addition and a dehydrobromination under DABCO assistance.

Cited by 6 publications

References 76 publications

Regioselective Halogenation of 2H‐Chromenones Promoted by Oxone and NaX: A Facile Approach for the Preparation of Halochromenones and 2H‐Chromenone Natural Products

Regioselective Halogenation of 2H‐Chromenones Promoted by Oxone and NaX: A Facile Approach for the Preparation of Halochromenones and 2H‐Chromenone Natural Products

DABCO-mediated synthesis of aromatic esters from phenols, naphthols or 3-hydroxypyridines and aryl acyl peroxides at room temperature

Decarboxylative Iodination of Coumarin‐3‐carboxylic Acids: A Facile Access to 3‐Iodocoumarins

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