Rapid and catalyst free synthesis of new bis(benzo[g]chromene) and bis(pyrano[3,2-c]chromene) derivatives and optimization of reaction conditions using response surface methodology

Abstract

Rapid and catalyst free synthesis of new bis(benzo [g]chromene) and bis(pyrano[3,2-c]chromene) derivatives and optimization of reaction conditions using response surface methodology † Fahimeh Sadat Hosseini, Mohammad Bayat * and Milad Afsharnezhad 4,4 0 -(1,4-phenylene)bis(2-(alkylamino)-3-nitro-4H-benzo[g]chromene-5,10-dione) and 4,4 0 -(1,4phenylene)bis(2-(alkylamino)-3-nitropyrano[3,2-c]chromen-5(4H)-one) derivatives are synthesized by a one-pot, multi-component reaction of N-alkyl-1-(methylthio)-2-nitroethenamine (derived from the reaction of various amines and 1,1-bis(methylthio)-2-nitroethene) with terephthalaldehyde or isophthalaldehyde, and 2-hydroxy-1,4-naphthoquinone or 4-hydroxycoumarin in EtOH/H 2 O (85 : 15) as the solvent at 89 C. Response surface methodology (RSM) is used to investigate the effect of reaction temperature and water content of aqueous ethanol on the product yields and reaction time. The notable features of this work are the optimization of reaction conditions with minimal experiments, absence of catalyst, good yields, simple work-up and the non-chromatographic purification of products. ; Tel: +98 28 33780040 † Electronic supplementary information (ESI) available. See a Various amines (2 mmol), 1,1-bis(methylthio)-2-nitroethene (2 mmol), phthalaldehyde (1 mmol), 2-hydroxy-1,4-naphthoquinone (2 mmol) and 4hydroxycumarin (2 mmol) were used. The reactions were run in EtOH/H 2 O (85 : 15) at 89 C, without any catalyst.Scheme 5 Proposed mechanism for the synthesis of product 6.This journal is

Insights into the Origin and Therapeutic Implications of Benzopyran and Its Derivatives

“…All compounds mix with dilute alcohol as a solvent at 89 °C. In the reaction mixture, hydroxy‐naphthoquinone was added to form dimer pyranonaphthoquinone while hydroxy‐coumarin was added to form dimer pyranocoumarin [32,38] . 5‐oxo‐5,6,7,8‐tetrahydro‐4H‐benzo‐[b]‐pyran derivative has been synthesized from perfluorooctanoate [RE(PFO) 3 ] catalyzes facile condensation of dimedone, aldehydes, and malononitrile under mild conditions [150] .…”

“…Benzopyran synthesis methods are challenging due to the restriction of substitution addition. [32][33][34][35] Chromium complex tridentate chiral catalyst shows Schiff base property to form Oxa [4 + 2] Cycloaddition and allylboration by the reaction of 2-Substituted Enol Ether with 1,3-dienylboronates. Produced cyclic allylic boronates further react with substituted aldehyde up to 110 °C to form pyran derivatives.…”

“…[103] 2-amino-4-aryl-4H-chromene regulates aminopeptidase inhibitor which has a wide range of therapeutic activities. The substituent benzopyran 4-(pyridine-3yl) or 4-(isoquinolin-3-yl) and 2-amino or 2acetamido like (E)-ethyl 2-amino-4-(1-aminobuta-1,3-dien-2-yl)-7-hydroxy-4H-chromenes-3-carboxylate (HF1-142) (32),(E)-ethyl2-acetamido-4-(1-aminobuta-1,3-dien-2-yl)-7-hydroxy-4Hchromene-3-carboxylate (HF1-419) (33), ethyl 2-amino-7hydroxy-4-(quinolin-3-yl)-4H-chromene-3-carboxylate (HF1-435) (34), ethyl 2-acetamido-7-hydroxy-4-(quinolin-3-yl)-4H-chromene-3-carboxylate (HF1-437) (35) are used as a most potential IRAP inhibitors. [104] Moreover, derivatives of amino benzopyran possessed vast application in various fields such as pigments, cosmetic and biodegradable agrochemicals, their structures are described in Figure 4.…”

“…In the reaction mixture, hydroxy-naphthoquinone was added to form dimer pyranonaphthoquinone while hydroxy-coumarin was added to form dimer pyranocoumarin. [32,38] conditions. [150] The benzopyran and pyran derivatives have been synthesized from 1,3-dicarbonyl compounds, aldehydes, and malononitrile in various solvents based on choline chloride.…”

New Insights Into the Origin and Therapeutic Implications of Benzopyran and Their Derivatives: A Review

“…Myriad benzopyran derivatives, a synthetic process have been produced by cyclization via alkyne πactivation. Benzopyran synthesis methods are challenging due to the restriction of substitution addition [32], [33], [34], [35]. Chromium complex tridentate chiral catalyst shows Schiff base property to form Oxa[4+2] Cycloaddition and allylboration by the reaction of 2-Substituted Enol Ether with 1,3dienylboronates.…”