4352-89-0Relevant academic research and scientific papers
Lewis acid-catalyzed annulative partial dimerization of 3-aryloxyacrylates to 4-arylchroman-2-ones: Synthesis of analogues of tolterodine, RORγ inhibitors and a GPR40 agonist
Kunkalkar, Rupesh A.,Fernandes, Rodney A.
supporting information, p. 2313 - 2316 (2019/02/27)
A beguiling annulative partial dimerization of 3-aryloxyacrylates to 4-arylchroman-2-ones catalyzed by Lewis acid (BF3·OEt2) has been developed. The reaction involves two molecules of 3-aryloxyacrylate, resulting in the loss of one propiolate molecule to furnish 4-arylchroman-2-one, an important structural motif found in many natural products. This methodology has been elaborated to synthesize analogues of tolterodine, RORγ inhibitors and a GPR40 agonist.
Photocyclization reactions of N-substituted 3-(2- hydroxynaphthalen-1-yl) propenamide derivatives accompanied by liberation of aliphatic and aromatic primary amines
Watanabe, Koh,Takahashi, Shun,Yoshizawa, Takuya,Igarashi, Tetsutaro,Sakurai, Tadamitsu
, p. 1503 - 1514 (2014/07/07)
(E)-3-(2-Hydroxynaphthalen-1-yl)propenoyl- and (E)-3-(2- hydroxynaphthalen-1-yl)-2-methylpropenoyl-protected aliphatic and aromatic primary amines were synthesized and their photolytic behavior in methanol was explored. The results showed that irradiation of the hydroxynaphthylpropenamide derivatives in a protic polar solvent at wavelengths greater than 280 nm or 340 nm causes rather efficient deprotection reactions to afford the desired amines quantitatively along with fluorescent benzocoumarins.
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.
