95025-74-4Relevant academic research and scientific papers
Tandem Alkyne Hydroacylation and Oxo-Michael Addition: Diastereoselective Synthesis of 2,3-Disubstituted Chroman-4-ones and Fluorinated Derivatives
Du, Xiang-Wei,Stanley, Levi M.
supporting information, p. 3276 - 3279 (2015/07/15)
Tandem reactions involving Rh-catalyzed intermolecular hydroacylations of alkynes with salicylaldehydes followed by intramolecular oxo-Michael additions are described for the diastereoselective synthesis of 2,3-disubstituted chroman-4-ones. The tandem hydroacylation/oxo-Michael additions occur to form 2,3-disubstituted chroman-4-ones in high yields from a range of 1,2-disubstituted acetylenes and substituted salicylaldehyes. The resulting 2,3-disubstituted chroman-4-ones are readily fluorinated to form trans-3-fluoro-2,3-disubstituted chroman-4-ones in high yields with excellent diastereoselectivity. (Chemical Equation Presented).
Synthesis, anticancer and antioxidant activities of 7-methoxyisoflavanone and 2,3-diarylchromanones
Kanagalakshmi, Kanagasabai,Premanathan, Mariappan,Priyanka, Ragunathan,Hemalatha, Balasubramanian,Vanangamudi, Arumugasamy
experimental part, p. 2447 - 2452 (2010/07/08)
A convenient, fast and high yielding method for the preparation of 7-methoxyisoflavanone and 2,3-diarylchromanones has been developed by the condensation of benzyl-2-hydroxy-4-alkoxyphenylketone with arylaldehyde/paraformaldehyde in presence of diethylamine, assisted by microwave activation. All the synthesized compounds were screened for anticancer as well as antioxidant activities. Among the nine compounds, 7-methoxyisoflavanone 7 and diarylchromanone 6c shows potential anticancer activity and diarylchromanone 6b has potential antioxidant activity. Compound 6h possesses anticancer and antioxidant activity at the same concentration.
Synthesis of 2,3-trans-3,4-trans-2-aryl-3-alkyl/aryl chroman-4-ols
Venkati,Krupadanam, G. L. David
, p. 618 - 621 (2007/10/03)
α-Alkyl chalcones 3a-d on acid catalyzed cyclization give a mixture of (±) trans and (±) cis 2-aryl-3-alkylchroman-4-ones. cis 4a-d are converted to trans 5a-d by epimerization with dil. alkali. α-Aryl chalcones 3e-h on acid catalyzed cyclization give (±) trans 2,3-diaryl-chroman-4-ones 5e-h. On NaBH4 reduction 5a-h give (±) 2,3-trans-3,4-trans-2-aryl-3-alkyl/aryl- chroman-4-ols 6a-h.
Synthesis of 3-aryl-1-(4-methoxyphenyl)-2--2-propen-1-ones and benzopyran derivatives
Verma, Braham S.,Dhindsa, Kuldip Singh,Sangwan, Naresh K.
, p. 239 - 243 (2007/10/02)
Acylation of anisole (5) or m-methoxyphenol (6) with arylacetic acid (7 or 8) gives the corresponding deoxybenzoins (9-12) along with minor isomeric product 13 in one case.Acetylation of 4-hydroxy-4'-methoxydeoxybenzoin (10) with acetic anhydride in pyridine or its alkylation with N-(2-chloroethyl)diethylammonium/pyrrolidinium chloride furnishes the corresponding deoxybenzoin derivatives (14-16).Condensation of 9, 11, 15 and 16 with araldehydes affords the corresponding title compounds 2-propen-1-ones (17, 19 and 21-23). 1-(2-Hydroxy-4-methoxyphenyl)-2,3-diphenyl-2-propen-1-one (19) is isomerized using silica gel or hydrochloric acid to 2,3-trans-2,3-dihydro-7-methoxy-2,3-diphenyl-4H-1-benzopyran-4-one (24) which on sodium borohydride reduction provides a mixture of isomeric benzopyranols (25).Dehydration of 25 gives 7-methoxy-2,3-diphenyl-2H/4H-1-benzopyran (27).The isomeric 7-methoxy-2,4-diphenyl-2H/4H-1-benzopyran (28) is prepared by the reaction of 2,3-dihydro-7-methoxy-2-phenyl-4H-1-benzopyran-4-one (26) with phenylmagnesium bromide.Condensation of 11 with 7 in acetic anhydride/triethylamine furnishes 4-benzyl-7-methoxy-3-phenyl-2H-1-benzopyran-2-one (29).
