Synthetic application of lithiation reactions-XVI : syntheses of (±) tetrahydropalmatine, (±) canadine, (±) stylopine and (±) sinactine
作者： N.S. Narasimhan , R.S. Mali , B.K. Kulkarni
DOI: 10.1016/S0040-4020(01)91915-5
关键词:
摘要: N,N-Dimethyl-3,4-dimethoxy- and methylenedioxybenzylamines were lithiated the organolithium intermediates treated with paraformaldehyde to give 2-hydroxymethyl derivatives. The latter converted 7,8-dimethoxy- methylenedioxyisochroman-3-ones through successive reaction ClCOOEt, KCN KOH. isochromanones on condensation homoveratrylamine or homopiperonylamine, followed by cyclisation reduction furnished protoberberine alkaloids.
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sci-hub.se 参考文章(39)
N.S. Narasimhan, B.H. Bhide, Synthetic applications of lithiation reactions-V : novel synthesis of methoxy isocoumarins. Synthesis of (±) mellein Tetrahedron. ,vol. 27, pp. 6171- 6176 ,(1971) , 10.1016/S0040-4020(01)91782-X
N.S. Narasimhan, P.S. Chandrachood, N.R. Shete, Synthetic application of lithiation reactions—xiv : Novel synthesis of 7,8-dimethoxy phenanthridine Tetrahedron. ,vol. 37, pp. 825- 827 ,(1981) , 10.1016/S0040-4020(01)97703-8
N.S. Narasimhan, R.S. Mali, Synthetic application of lithiation reactions—VII Tetrahedron. ,vol. 31, pp. 1005- 1009 ,(1975) , 10.1016/0040-4020(75)80118-9
N.S. Narasimhan, R.S. Mali, Synthetic application of lithiation reactions—VI Tetrahedron. ,vol. 30, pp. 4153- 4157 ,(1974) , 10.1016/S0040-4020(01)97400-9
Walter H. Puterbaugh, Charles R. Hauser, Metalation of N-Methylbenzamide with Excess n-Butyllithium. Condensations with Electrophilic Compounds to Form ortho Derivatives. Cyclizations1 Journal of Organic Chemistry. ,vol. 29, pp. 853- 856 ,(1964) , 10.1021/JO01027A020
Frank N. Jones, Mary F. Zinn, Charles R. Hauser, Metalations of Benzyldimethylamine and Related Amines with n-Butyllithium in Ether. Deuteration to Form Ring and Side-chain Derivatives1 Journal of Organic Chemistry. ,vol. 28, pp. 663- 665 ,(1963) , 10.1021/JO01038A014
Amé Pictet, Alfons Gams, Synthese des Berberins Berichte der deutschen chemischen Gesellschaft. ,vol. 44, pp. 2480- 2485 ,(1911) , 10.1002/CBER.19110440372
H. Suguna, B. R. Pai, Synthesis of tetrahydrogroenlandicine, a protoberberine alkaloid Collection of Czechoslovak Chemical Communications. ,vol. 41, pp. 1219- 1224 ,(1976) , 10.1135/CCCC19761219
C.-Y. Chen, D. B. MacLean, Mass spectra and proton magnetic resonance spectra of some tetrahydroprotoberberine alkaloids Canadian Journal of Chemistry. ,vol. 46, pp. 2501- 2506 ,(1968) , 10.1139/V68-410
J. M. Mallan, R. L. Bebb, Metalations by organolithium compounds Chemical Reviews. ,vol. 69, pp. 693- 755 ,(1969) , 10.1021/CR60261A006