19076-56-3Relevant academic research and scientific papers
Two practical syntheses of an anti-inflammatory sesquiterpene furoic acid from Sinularia spp.
Williams,Faulkner
, p. 4245 - 4256 (1996)
The sesquiterpene (1'E,5'E)-2-(2',6'-dimethylocta-1',5',7'-trienyl)-4-furoic acid (2), which is an anti-inflammatory metabolite of the soft coral Sinularia spp. has been synthesized by two routes, both of which employ a Claisen rearrangement.
Synthesis of 2,3-dicarbonylated pyrroles and furans via the three-component Hantzsch reaction
Moss, Thomas A.,Nowak, Thorsten
scheme or table, p. 3056 - 3060 (2012/08/08)
Pyrroles containing a 2,3-dicarbonyl substitution pattern are synthesized in one step via a three-component Hantzsch procedure. The normally difficult-to-access substrates are readily obtained in short reaction times and in moderate to good yields, giving pharmaceutically attractive products containing multiple handles for further elaboration.
Isoindolone formation via intramolecular Diels-Alder reaction
Ball, Matthew,Boyd, Alistair,Churchill, Gwydion,Cuthbert, Murray,Drew, Mark,Fielding, Mark,Ford, Gair,Frodsham, Lianne,Golden, Michael,Leslie, Kevin,Lyons, Sarah,McKeever-Abbas, Ben,Stark, Andrew,Tomlin, Paula,Gottschling, Stephen,Hajar, Abraham,Jiang, Ji-Long,Lo, Josephine,Suchozak, Bob
experimental part, p. 741 - 747 (2012/07/31)
The intramolecular Diels-Alder reaction provides a useful synthetic methodology to build biologically active and synthetically useful isoindolone ring systems. An application of this methodology, providing an efficient manufacturing route to an mGluR2 positive allosteric modulator via a 1,5,7-substituted isoindolone, is reported herein.
Intra-molecular Diels-Alder reactions of citraconamic acids from furfurylamines and citraconic anhydride: Effects of substitution in the furan ring on regioselectivity
Murali, Rajappa,Surya Prakash Rao,Scheeren, Hans W
, p. 3165 - 3174 (2007/10/03)
Regioselectivity in the intra-molecular Diels-Alder (IMDA) reaction of furfurylcitraconamic acids derived from N-benzylfurfurylamines and citraconic anhydride can be controlled by substituents located in the furan ring and by reaction conditions. Reactions conducted under kinetic conditions resulted in cycloaddition products having methyl and aminomethylene substituent in 1,3-relationship whereas under thermodynamic conditions, excepting in the case of the 3-methylsulfanyl group, the products rearranged to more stable cycloadducts in which the substituents are in 1,2-relationship. Product formation can be explained on the basis of frontier orbital interactions and steric considerations.
