63523-19-3Relevant academic research and scientific papers
Stereoselective allylation and reduction of N-tert-butanesulfinyl-α-keto aldimines
Maciá, Edgar,Foubelo, Francisco,Yus, Miguel
, p. 1407 - 1413 (2017/10/06)
A simple methodology for the synthesis of N-tert-butanesulfinyl-α-keto aldimines from both α-keto aldehydes and carboxylic esters has been developed. The addition of an in situ formed allyl indium reagent to these chiral imines was also studied. The addition took place in a sequential manner, first to the imine group with excellent diastereoselectivity and then to the carbonyl group with lower diastereoselectivity. Ruthenium-catalyzed ring closing metathesis of the resulting 5-aminoocta-1,7-dien-4-ol derivatives provided access to 6-aminocyclohex-3-enols. Reduction of the α-keto aldimines led to N-tert-butanesulfinyl-1,2-aminoalcohols as a 1:1 diastereomeric mixture.
Cyclocondensation of hydroxylamine with 1,3-bis(het)arylmonothio 1,3-diketones and 1,3-bis(het)aryl-3-(methylthio)-2-propenones: Synthesis of 3,5-bis(het)arylisoxazoles with complementary regioselectivity
Raghava, Byregowda,Parameshwarappa, Gangajji,Acharya, Anand,Swaroop, Toreshettahally R.,Rangappa, Kanchugarakoppal S.,Ila, Hiriyakkanavar
, p. 1882 - 1892 (2014/04/03)
Efficient routes for the regioselective synthesis of 3,5-bis(het) arylisoxazoles with complementary regioselectivity have been developed. The methods involve the cyclocondensation of hydroxylamine hydrochloride with either 1,3-bis(het)aryl-monothio-substituted 1,3-diketones 1 or with 3-methylthio-1,3-bis(het)aryl-2-propenones 2 under various reaction conditions. In the first protocol, diketones 1 were treated with hydroxylamine hydrochloride in the presence of sodium acetate/acetic acid (pH 2.2) in refluxing ethanol/benzene to give 3,5-bis(het)arylisoxazoles 5, in which the het(aryl) moiety attached to thiocarbonyl group of the monothio-substituted 1,3-diketones is installed at the 3-position. On the other hand, the reaction of hydroxylamine hydrochloride with 3-(methylthio)-1,3-bis(het)aryl-2-propenones 2 in the presence of barium hydroxide in refluxing ethanol gave 3,5-bis(het) arylisoxazoles 6 with complementary regioselectivity in high yields. A probable mechanism for the formation of regioisomeric isoxazoles 5 and 6 from precursors 1 and 2 has been suggested.
Cyclocondensation of Hydroxylamine with 1,3-Bis(het)arylmonothio 1,3-Diketones and 1,3-Bis(het)aryl-3-(methylthio)-2-propenones: Synthesis of 3,5-Bis(het)arylisoxazoles with Complementary Regioselectivity
Raghava, Byregowda,Parameshwarappa, Gangajji,Acharya, Anand,Swaroop, Toreshettahally R.,Rangappa, Kanchugarakoppal S.,Ila, Hiriyakkanavar
, p. 1882 - 1892 (2015/10/05)
Efficient routes for the regioselective synthesis of 3,5-bis(het)arylisoxazoles with complementary regioselectivity have been developed. The methods involve the cyclocondensation of hydroxylamine hydrochloride with either 1,3-bis(het)aryl-monothio-substituted 1,3-diketones 1 or with 3-methylthio-1,3-bis(het)aryl-2-propenones 2 under various reaction conditions. In the first protocol, diketones 1 were treated with hydroxylamine hydrochloride in the presence of sodium acetate/acetic acid (pH 2.2) in refluxing ethanol/benzene to give 3,5-bis(het)arylisoxazoles 5, in which the het(aryl) moiety attached to thiocarbonyl group of the monothio-substituted 1,3-diketones is installed at the 3-position. On the other hand, the reaction of hydroxylamine hydrochloride with 3-(methylthio)-1,3-bis(het)aryl-2-propenones 2 in the presence of barium hydroxide in refluxing ethanol gave 3,5-bis(het)arylisoxazoles 6 with complementary regioselectivity in high yields. A probable mechanism for the formation of regioisomeric isoxazoles 5 and 6 from precursors 1 and 2 has been suggested.
