63023-79-0Relevant academic research and scientific papers
EVIDENCE FOR A CHARGE-TRANSFER MECHANISM IN THE PHOTO-OXYGENATION OF AN ENAMINE
Martin, Ned H.,Jefford, Charles W.
, p. 3949 - 3952 (1981)
Evidence for a charge-transfer mechanism in the photo-oxygenation of the enamine form of 1-benzyl-3,4-dihydroisoquinolines is presented.Substituent effects, normalized to constant enamine concentration, fit best a mechanism involving the formation of a ra
Synthesis of isoquinoline alkaloids via oxidative amidation-bischler- napieralski reaction
Shankar,More, Satish S.,Madhubabu,Vembu,Syam Kumar
supporting information; experimental part, p. 1013 - 1020 (2012/06/01)
A straightforward synthesis of -keto amides by coupling primary amines with aryl dibromoethanones under oxidative amidation conditions has been developed. The -keto amides were then subjected to heterocyclodehydration reaction under Bischler-Napieralski conditions followed by aromatization with DBU provided 1-benzoyl isoquinolines in a two-stage process. Utilizing this methodology, isoquinoline alkaloids such as thalmicrinone, papavaraldine, and pulcheotine A were synthesized in excellent yields. Georg Thieme Verlag Stuttgart · New York.
Desulfonylation of N-sulfonyl tetrahydroisoquinoline derivatives by potassium fluoride on alumina under microwave irradiation: Selective synthesis of 3,4-dihydroisoquinolines and isoquinolines
Silveira, Claudio C.,Bernardi, Carmem R.,Braga, Antonio L.,Kaufman, Teodoro S.
, p. 907 - 910 (2007/10/03)
In a solvent-free system, the microwave irradiation of mixtures of N-sulfonyl tetrahydroisoquinolines and 37% potassium fluoride supported on alumina selectively furnished 3,4-dihydroisoquinolines or isoquinolines, depending upon the reaction time.
Oxidation of 1-Benzyl-3,4-dihydroisoquinolines Using Active Manganese Dioxide
Amaravathi, M.,Kumari, L. Krishna,Pardhasaradhi, M.
, p. 1246 - 1247 (2007/10/02)
Oxidation of 1-benzyl-3,4-dihydroisoquinolines (I, IV-VII) by active MnO2 affords the corresponding 1-benzoyl-3,4-dihydroisoquinolines in yields >80percent, except in the case of VI which gives the oxidation product in 46percent yield.
Synthesis and Photo-oxygenation of Some Substituted 1-Benzyl-3,4-dihydroisoquinolines. Mechanism of Enamine Photo-oxygenation
Martin, Ned H.,Jefford, Charles W.
, p. 762 - 774 (2007/10/02)
The synthesis of a series of substituted 1-benzyl-3,4-dihydroisoquinolines by Bischler-Napieralski cyclization is described.Competitive methylene blue sensitized photo-oxygenation experiments allowed the determination of relative rates of photo-oxygenation of 1-benzyl-3,4-dihydroisoquinolines.Substituents were shown to affect both the equilibrium concentration of the tautomeric enamine and the overall photo-oxygenation rate.After correcting for differences in enamine concentration, the relative rate data provided a diagnostic probe of the reaction mechanism, which involves transfer of charge in the rate-limiting step.
Self-Sensitized Photo-Oxidation of 1-Benzyl-3,4-dihydroisoquinolines
Martin, Ned H.,Jefford, Charles W.
, p. 2189 - 2192 (2007/10/02)
The air oxidation of 1-benzyl-3,4-dihydroisoquinolines is shown to be a self-sensitized photo-oxidation proceeding via singlet oxygen.
REGIOPSPECIFIC OXIDATION OF SUBSTITUTED 1-BENZYL-3,4-DIHYDROISOQUINOLINES USING SINGLET OXYGEN
Martin, Ned H.,Champion, Sidney L.,Belt, Phillip B.
, p. 2613 - 2616 (2007/10/02)
Singlet oxygen regiospecifically oxidizes 1-benzyl-3,4-dihydroisoquinoline to 1-benzoyl-3,4-dihydroisoquinoline.Mechanistic studies do not distinguish between a dioxetane or the alternative zwitterionic peroxide intermediate.
