80541-54-4Relevant academic research and scientific papers
Acylation of Aldo 1-Pyrroline 1-Oxides (4,5-Dihydro-3H-pyrrole 1-Oxides) and the Oxidation of the Resulting 3-Acyloxy-1-pyrrolines (3-Acyloxy-4,5-dihydro-3H-pyrroles)
Gibson, Neil J.,Forrester, Alexander R.
, p. 491 - 500 (2007/10/02)
5,5-Dimethyl-1-pyrroline 1-oxide (DMPO), when treated with NaH (1 mol) followed by ethyl chloroformate, benzoyl chloride, pivaloyl chloride or 2-bromoisobutyryl bromide gave the corresponding 3-acyloxy-1-pyrrolines.With NaH (2-4 mol) followed by benzoyl chloride or 2-bromoisobutyryl bromide, DMPO gave the corresponding 2-(3'-acyloxy-1'-pyrrolin-3'-yl)-3-acyloxypyrrolidines.Acylation of the 3-phenyl and 3-methyl DMPOs also gave the corresponding 3-acyloxy-1-pyrrolines.Oxidation of the 3-acyloxy-1-pyrrolines with m-CPBA gave the correspondong oxaziridines in good yield.These oxaziridines were resistant to ring opening by acid hydrolysis, photolysis and thermolysis.
Photochemical Nitrogen Extrusion of 5-Amino-1-vinyl-4,5-dihydro-1H-1,2,3-triazoles. Formation of Unusual Pyrroles
Ito, Masato M.,Nomura, Yujiro,Takeuchi, Yoshito,Tomoda, Shuji
, p. 533 - 536 (2007/10/02)
Photolysis of 4-alkyl-5-amino-1-vinyl-4,5-dihydro-1H-1,2,3-triazoles gave not 3-alkylpyrroles, but unexpected 2-alkylpyrroles in 80-83percent yields. 1-Vinylaziridines were assumed as a possible intermediate of this unusual pyrrole formation.In the photol
5-Amino-1-vinyl-4,5-dihydro-1H-1,2,3-triazoles as a Source of 1-Amino-2-aza-1,3-butadiene
Nomura, Yujiro,Takeuchi, Yoshito,Tomoda, Shuji,Ito, Masato M.
, p. 2779 - 2785 (2007/10/02)
Thermolysis of 4,4-dimethyl-1-(1-phenylvinyl)-5-(1-pyrrolidinyl)-4,5-dihydro-1H-1,2,3-triazole gave 2-methyl-N-(1-phenylvinyl)-1-(1-pyrrolidinyl)-1-propanimine, which reacted as a 2-azabutadiene with electrondeficient dienophiles to afford the corresponding cycloadducts.Reactivity and regioselectivity of the cycloaddition reactions were rationalized with the frontier molecular orbital treatment.
FORMATION OF UNUSUAL PYRROLES BY PHOTOLYSIS OF 1-VINYL-4,5-DIHYDRO-1H-1,2,3-TRIAZOLES
Ito, Masato M.,Nomura, Yujiro,Takeuchi, Yoshito,Tomoda, Shuji
, p. 1519 - 1522 (2007/10/02)
Photolysis of 4-alkyl-5-amino-1-vinyl-4,5-dihydro-1H-1,2,3-triazoles gave not 3-alkylpyrroles but unexpected 2-alkylpyrroles in 80-83 percent yields.Similarly, 4,4-dimethyltriazole derivatives gave 2,2-dimethyl-2H-pyrroles in 70-74 percent yields. 1-Vinylaziridines were assumed as a possible intermediate of this anomalous reaction.
