54107-67-4

Usage

InChI:InChI=1/C14H10O4/c1-7-3-13(15)17-11-6-12-10(5-9(7)11)8(2)4-14(16)18-12/h3-6H,1-2H3

Upstream product

• 90-33-5 7-hydroxy-4-methyl-chromen-2-one 
• 16555-98-9 6-acetyl-7-hydroxy-4-methylcoumarin 
• 1099-45-2 ethyl (triphenylphosphoranylidene)acetate 
• 141-97-9 ethyl acetoacetate 
• 108-46-3 recorcinol 
• 2161-85-5 1-(5-acetyl-2,4-dihydroxyphenyl)-1-ethanone 
• 108-24-7 acetic anhydride 
• 154519-48-9 ethyl E-3-(7-hydroxy-4-methyl-2-oxo-2H-1-benzopyran-6-yl)-2-butenoate 

Relevant academic research and scientific papers

4,6-DIMETHYL-2H, 8H-BENZODIPYRAN-2,8-DIONE.FORMATION OF LINEAR AND ANGULAR ISOMERS IN THE PECHMANN REACTION

The structure of Hantzsch and Zuerchers "dimethyldicoumarin" obtained from resorcinol or 7-hydroxy-4-methylcoumarin and ethylacetatoacetate has been confirmed as the linear title compound 1. peri-Substituent effects in 1H and 13C NMR spectroscopy have been used to differentiate between the lin and ang isomers, the ang Me groups being deshielded.A set of rules to govern the formation of lin/ang isomers has been proposed.

The structure of Hantzsch coumarin

The dimethyl dicoumarin prepared by Hantzsch and Zurcher has been characterized as 4,6-dimethyl-2H,8H-benzo[1,2-b:4,5-b′]dipyran-2,8-dione by unambiguous synthesis of both angular (2a) and linear (2b) pyranocoumarins by Wittig reaction promoted by clay and comparing them with authentic Hantzsch coumarin prepared as described in literature. This is the first record of synthetic proof for the structure of Hantzsch coumarin.

A new method for annulation of the α-pyrone ring

New derivatives of coumarin, containing annulated α-pyrone rings, were obtained by reaction of the borate complexes of three isomeric acyl(hydroxy)coumarins with acid anhydrides. It was shown that the borate complex of 3-acetyl-4-hydroxy-2-pyrone also condenses with acetic anhydride to form a derivative containing a new annulated α-pyrone ring.

Reactions of 4,6-Bis(acetyl)resorcinol with Alkoxycarbonylalkylidene(triphenyl)phosphoranes. Preparation of Coumarin Derivatives

Reaction of compound 1 with ylide 2a affords compounds 3a,3b and coumarins 4a,5a, 5b, 6a in 77percent total yield.Reaction of 1 with ylide 2b affords coumarin 4b.The acetylderivatives obtained, react further with ylides 2a-c to give pyranochromene-2,8-diones 6b-d.

Synthesis of Linear and Angular Benzodipyrans

Synthesis of 2H,8H-4,6-dimethylbenzodipyran-2,8-dione(I) and the isomeric 2H,8H-4,10-dimethylbenzodipyran-2,8-dione(II) is described.The linear isomer(I) is identical with the neutral product obtained in the reaction of resorcinol with ethyl acetoacetate in presence of conc. sulphuric acid .