42251-12-7Relevant academic research and scientific papers
Synthesis of cucurbitine derivatives: facile straightforward approach to methyl 3-amino-4-aryl-1-methylpyrrolydine-3-carboxylates
Blanco-Ania, Daniel,Hermkens, Pedro H.H.,Sliedregt, Leo A.J.M.,Scheeren, Hans W.,Rutjes, Floris P.J.T.
supporting information; experimental part, p. 5393 - 5401 (2009/10/17)
A general three- or four-step synthesis of cis- and trans-substituted cucurbitine (3-aminopyrrolidine-3-carboxylic acid) derivatives from methyl 2-nitroacetate is reported. The first step utilizes a Knoevenagel condensation with five different aromatic imines or their corresponding aldehydes to form (Z/E)-mixtures of α-nitro acrylates. The second step gives rise to the pyrrolidine-core structures of the title compounds by a 1,3-dipolar cycloaddition reaction using an azomethine ylide. The last step consists of reduction of the nitro group to yield both diastereoisomers of the corresponding 4-aryl cucurbitine methyl esters.
Generation and application of o-Quinone methides bearing various substituents on the benzene ring
Sugimoto, Hiromichi,Nakamura, Satoshi,Ohwada, Tomohiko
, p. 669 - 679 (2008/02/09)
o-Quinone methides (o-QMs) are highly reactive, short-lived intermediates, which have potential synthetic applicability. However, few studies on the generation of o-QMs bearing an electron-withdrawing group have been reported. Herein we present a general method for the generation of o-QMs, particularly those substituted with an 0lectrophilic substituent, from new precursors, 4H-1,2-benzoxazines 2. We have also studied systematically the Diels-Alder reactions of o-QMs with various dienophiles, such as vinyl ethers, enamines and imines. The reactions provide a versatile route to substituted chromans, phenols and 3,4-dihydro-2H-benzo[e]-[1,3]oxazines (3,4-dihydro-1,3-benzoxazines). Furthermore, we applied the new method to the derivatization of some natural products.
REACTIONS DES METHYLAZIDE ET PHENYLAZIDE AVEC QUELQUES ALCYNES ET OLEFINES α-NITREES. SYNTHESE REGIOSPECIFIQUE DES 1,2,3 TRIAZOLES
Piet, J. C.,Hetet, G. Le,Cailleux, P.,Benhaoua, H.,Carrie, R.
, p. 33 - 44 (2007/10/03)
The reactions of alkynes and α-nitro-olefines with methylazide and phenylazide was studied.In contrast to known reactions with alkynes which are non-regioselective, methylazide and phenylazide react regiospecifically with α-nitro-olefines and give only one type of triazole after elimination of HNO2.These reactions are very useful synthetic approaches to 1,2,3 triazoles.
ALUMINA SUPPORTED POTASSIUM FLUORIDE PROMOTED REACTION OF NITROALKANES WITH ELECTROPHILIC ALKENES: SYNTHESIS OF 4,5-DIHYDRO FURANS AND ISOXAZOLINE N-OXIDES.
Melot, Jean Marie,Texier-Boullet, Francoise,Foucaud, Andre
, p. 2215 - 2224 (2007/10/02)
The reaction of secondary nitro alkanes 1 with α,β-unsaturated ketones 2 in the presence of alumina-supported potassium fluoride in acetonitrile gave 4,5-dihydrofurans 3 in high yields; 1-nitropropane reacted with 2 to give a mixture of 4,5-dihydrofurans and furans.Nitroalkenes 17 reacted with nitroalkanes to give isoxazoline N-oxides 18 and 19 in good overall yields.
PREPARATION AND Z-E ISOMERIZATION OF SUBSTITUTED NITROSTYRENES
Blaha, Ivo,Leseticky, Ladislav
, p. 1094 - 1099 (2007/10/02)
This study concerns the synthesis of β-substituted β-nitrostyrenes by two procedures: addition of nitryl halogenides to double bonds, connected with the elimination of hydrogen halide, and condensation of aldehydes with substituted nitromethanes, and it c
