197314-77-5Relevant academic research and scientific papers
Synthesis of Coumarins by Flash Vacuum Pyrolysis of 3-(2-Hydroxyaryl)propenoic Esters
Cartwright, Gary A.,McNab, Hamish
, p. 296 - 297 (1997)
Flash vacuum pyrolysis of 3-(2-hydroxyaryl)propenoic esters gives coumarins (and other fused α-pyrones) in high yieid.
Free radical scavenging and α-glucosidase inhibitory activity of (E)-methyl/ethyl-3-(2-hydroxyphenyl)acrylates
Harikrishna, G.,Hariprasad, K. Siva,Raju, B. China,Tiwari, A. K.,Zehra, A.
, p. 111 - 116 (2021/09/28)
(E)-Methyl/ethyl-3-(2-hydroxyphenyl)acrylates 3a-x have been prepared by the reaction of salicylaldehydes 1a-l with Wittig reagents such as methyl (triphenylphosphoranylidene)acetate 2a and ethyl (triphenylphosphoranylidene)acetate 2b in dry DCM at room t
Cyclization of ortho-hydroxycinnamates to coumarins under mild conditions: A nucleophilic organocatalysis approach
Boeck, Florian,Blazejak, Max,Anneser, Markus R.,Hintermann, Lukas
supporting information, p. 1630 - 1636,7 (2020/09/14)
(E)-Alkyl ortho-hydroxycinnamates cyclize to coumarins at elevated temperatures of 140-250 °C. We find that the use of tri-nbutylphosphane (20 mol %) as a nucleophilic organocatalyst in MeOH solution allows cyclization to take place under much milder conditions (60-70 °C). Several coumarins were prepared, starting from ortho-hydroxyarylaldehydes, by Wittig reaction with Ph3P=CHCO2Me to (E)-methyl ortho-hydroxycinnamates, followed by the phosphane catalyzed cyclization.
Task-specific ionic liquid as reagent and reaction medium for the one-pot Horner-Wadsworth-Emmons-type reaction under microwave irradiation
Valizadeh, Hassan,Shockravi, Abbas
experimental part, p. 4341 - 4349 (2010/04/26)
A task-specific imidazolium-based phosphinite ionic liquid (IL-OPPh2) was used as the dual solvent-reagent for the synthesis of E-cinamates and coumarin derivatives via the one-pot Horner-Wadsworth-Emmons-type reaction. The ionic liquid containing its cor
Convenient synthesis of a simple coumarin from salicylaldehyde and wittig reagent. IV: Improved synthetic method of substituted coumarins
Takeuchi, Yasuo,Ueda, Norihiro,Uesugi, Koji,Abe, Hitoshi,Nishioka, Hiromi,Harayama, Takashi
, p. 217 - 224 (2007/10/03)
The reaction of salicylaldehydes (2) with Horner-Wadsworth-Emmons (HWE) or Ando-HWE reagents was attempted to afford intramolecular phosphonate derivatives (6). A new synthetic method for coumarins (1) was achieved by using protected 2.
Synthesis of fused furans by gas-phase pyrolysis of 2-allyloxyaryl-propenoic esters
Black, Michael,Cadogan,McNab, Hamish,MacPherson, Andrew D.,Roddam, V. Peter,Smith, Carol,Swenson, Helen R.
, p. 2483 - 2493 (2007/10/03)
Flash vacuum pyrolysis of 2-allyloxypropenoic esters (e.g. 7) gives benzo[b]furans (e.g. 32) in synthetically useful yields by sequential generation of a phenoxyl radical, cyclisation and ejection of the carboxylic ester function as a free radical leaving group. The method is compatible with a range of substituents on either the benzene ring or the propenoate chain, and is particularly effective for 2-substituted benzo[b]furans. The natural products 5-methoxybenzo[b]furan 1 and angelicin 2 have been synthesised in three and four steps respectively from commercially available starting materials by this route. Related cyclisations to give naphtho[2,1-b]furan 40 were complicated by competitive formation of naphtho[2,1-b]pyran-3-ones (e.g. 41 and 42), but the yield of the required product could be optimised by the choice of the radical precursor. Annelation of a furan ring onto a thlophene is also possible by this method, but lower yields are obtained in such pyrolyses.
