102301-80-4Relevant academic research and scientific papers
A MECHANISTIC STUDY ON THE PHOTOCHEMICAL CYCLIZATION OF PROTONATED 2-AZA-1,3-DIENE DERIVATIVES
Armesto, Diego,Ortiz, Maria J.,Horspool, William M.,Romano, Santiago
, p. 374 - 379 (2007/10/03)
Quantum yield determinations for the photocyclization of protonated 4-aroyloxy-3,4-diaryl-1,1-diphenyl-2-azabuta-1,3-dienes 5 into substituted 3-aryl-1,1-diphenyl-isoquinolin-4(1H)-ones 6 support the involvement of an intramolecular single electron transfer (SET) mechanism from an aryl group to an iminium system. - Key words: Photochemistry; 2-Aza-1,3-dienes; Iminium salts; Isoquinolinones; Single electron transfer.
Reaction of Anions from Monoimines of Benzil with Alkylating Agents. Photochemical Reactivity of Some 4-Alkoxy-2-aza-1,3-dienes
Armesto, Diego,Horspool, William M.,Ortiz, Maria J.,Romano, Santiago
, p. 171 - 176 (2007/10/02)
The reaction of benzil benzhydrylmonoimine 6a with methyl iodide or dimethyl sulphate as the electrophile affords 4-alkoxy-2-aza-1,3-dienes resulting from an O-alkylation.When benzyl chloride is employed, products of O-alkylation C-alkylation and cyclization are produced, while with toluene-p-sulphonyl chloride only cyclization to a dihydro-oxazole takes place.Benzil α-phenylethylmonoimine 6b yields only products of C- and/or O-alkylation.In one case, when a large excess of dimethyl sulphate is used, cyclization affords N-methyl-2,3,5-triphenylpyrrole.Irradiation of the O-alkylated compounds (E)- and (Z)-4-methoxy-1,1,3,4-tetraphenyl-2-azabuta-1,3-diene and (E)-4-benzyloxy-1,1,3,4-tetraphenyl-2-azabuta-1,3-dienes in the presence of perchloric acid yields isoquinoline derivatives by a photo-Mannich reaction.
A Synthesis of Isoquinolinones by the Photochemical Cyclization of 2-Azabuta-1,3-dienes in the Presence of Acids
Armesto, Diego,Gallego, Mar G.,Ortiz, Maria J.,Romano, Santiago,Horspool, William M.
, p. 1343 - 1347 (2007/10/02)
A study of the photochemical reactions of a series of 2-azabuta-1,3-dienes in the presence of perchloric acid or boron trifluoride-diethyl ether is reported.The photochemical reaction affords cyclization of all of the dienes to yield novel isoquinolinone derivatives.The reaction is interpreted as involving protonation, or complexation of the nitrogen lone pair.This prevents an electron transfer reaction which has been reported to yield novel dihydro-oxazole derivatives.Instead a photochemical Mannich reaction results in cyclization with the production of the isoquinolinone skeleton.
A NEW SYNTHESIS OF 1,1-DIPHENYL-3-ARYLISOQUINOLIN-4-ONES BY THE NOVEL CYCLIZATION OF 2-AZABUTA-1,3-DIENES
Armesto, Diego,Horspool, William M.,Langa, Fernando,Ortiz, Maria J.,Perez-Ossorio, Rafael,Romano, Santiago
, p. 5213 - 5216 (2007/10/02)
The facile synthesis of novel 1,1-diphenyl-3-arylisoquinolin-4-ones by the cyclization of protonated 2-azabuta-1,3-dienes is reported.
