Regular Issue

Vol. 3, No. 4, 1975

8 data found. 1 - 8 listed
Communication | Regular issue | Vol 3, No. 4, 1975, pp. 283 - 286
Published online:
DOI: 10.3987/R-1975-04-0283
Mass Spectra of 3,4-Dihydro-4-imino-3-methylpyrimidines, Their Methylamino-isomers, and Related Systems

Desmond J. Brown* and Kazuharu Ienaga

*John Curtin School of Medical Research, Canberra City 2601, Australia


Those 3,4-dihydro-4-imino-3-methylpyrimidines and related systems, which undergo rapid Dimroth rearrangement in solution, have mass spectra indistinguishable from their methylaminoisomers. Similar imines, which do not rearrange easily, have their own fragmentation patterns. 4-Methylamino, methoxy, methylthio, and hydroxymethyl derivatives of pyrimidine and quinazoline, as well as the corresponding 6-substituted purines, have a common fragmentation pathway, hitherto unrecognized.

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Communication | Regular issue | Vol 3, No. 4, 1975, pp. 287 - 291
Published online:
DOI: 10.3987/R-1975-04-0287
Reactions of Pyridine N-Oxide with Enamines of N-Substituted 4-Piperidones in the Presence of an Acylating Agent

Michio Nakanishi, Masahiro Yatabe, and Masatomo Hamana*

*Faculty of Pharmaceutical Sciences, Kyushu University, 3-1-1 Maidashi, Higashi-ku, Fukuoka 812-8582, Japan


Pyridine N-oxide reacts with enamines of N-benzoyl-, N-ethoxycarbonyl- and N-acetyl-4-piperidones in the presence of benzoyl chloride to give N-substituted 3-(2-pyridy1)-4-piperidones in fair or good yields. Enamine of N-methyl- or N-benzyl-4-piperidone resists this reaction.

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Communication | Regular issue | Vol 3, No. 4, 1975, pp. 293 - 296
Published online:
DOI: 10.3987/R-1975-04-0293
Reaction of 2-Substituted 6-Methyl-4H-1,3-oxazin-4-one Derivatives with Enamine

Tetsuzo Kato,* Yutaka Yamamoto, and Masatsugu Kondo

*Pharmaceutical Institute, Tohoku University, Aobayama, Sendai 980-8578, Japan


Reaction of 1-(1-cyclopenten-1-yl)pyrrolidine (IIa) with 6-methyl-2-phenyl-4H-1,3-oxazin-4-one (Ia), 2-ethoxy-2,6-dimethyl-3,4-dihydro-2H-1,3-oxazin-4-one (Ib), and 2-benzyl-2-ethoxy-6-methyl-3,4-dihydro-2H- 1,3-oxazin-4-one (Ic) gave rise to 4-acetyl-3-hydroxy-1-phenyl-6,7-dihydro-5H-2-pyrindine (IIIa), 4-acetyl-3-hydroxy-1-methyl-6,7-dihydro-5H-2-pyrindine (IIIb), and 4-acetyl-1-benzyl-3-hydroxy-6,7-dihydro-4H-2-pyrindine (IIIc), respectively.
Similar reaction of 1-(1-cyclohexen-1-yl)pyrrolidine (IIb) with Ia afforded 4-acetyl-3-hydroxy-1-phenyl-5,6,7,8-tetrahydroisoquinoline (IV).

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Communication | Regular issue | Vol 3, No. 4, 1975, pp. 297 - 300
Published online:
DOI: 10.3987/R-1975-04-0297
The Origin of the Methylenoxy Bridge in Some Isoquinoline Alkaloids

Maurice Shamma* and Jerome L. Moniot

*Department of Chemistry, The Pennsylvania State University, York Campus, P1031 Edgecomb Avenue, York, Pennsylvania 17403, U.S.A.


The isolation of nantenine methochloride (1) from T. polygamum points to an oxonium ion being involved in the biogenesis of the methylenoxy bridge of thalphenine (3). Oxonium ions are also implicated in the formation of insularine (7), cissampareine (9), and reponduline (12).

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Communication | Regular issue | Vol 3, No. 4, 1975, pp. 301 - 305
Published online:
DOI: 10.3987/R-1975-04-0301
Structural Elucidation of Two New Spirobenzylisoquinoline Alkaloids, Yenhusomine and Yenhusomidine

Sheng-Teh Lu,* Tsann-Long Su, Tetsuji Kametani, and Masataka Ihara

*School of Pharmacy, Kaohsiung Medical College, 100 Shih Chuen 1st Rd., Kaohsiung 80708, Taiwan, R.O.C.


Yenhusomine and yenhusomidine, isolated from Corydalis ochotensis Turcz. (Papaveraceae) together with protopine, ochotensimine, and adlumidine, were assigned structures (3) and (4), respectively.

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Communication | Regular issue | Vol 3, No. 4, 1975, pp. 307 - 309
Published online:
DOI: 10.3987/R-1975-04-0307
Synthesis of N-Demethylfagaronine

Ichiya Ninomiya,* Takeaki Naito, and Hisashi Ishii

*Kobe Women’s College of Pharmacy, Motoyamakita, Higashinad, kobe, Hyogo658, Japan


N-Demethylfagaronine (II) was synthesized by the route including the enamide photocyclization.

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Review | Regular issue | Vol 3, No. 4, 1975, pp. 311 - 341
Published online:
DOI: 10.3987/R-1975-04-0311
Synthesis of the 1,2,3,4-Tetrahydroisoquinolines and Related Compounds by Phenolic Cyclisation

Tetsuji Kametani,* Keiichiro Fukumoto, Kazuo Kigasawa, Mineharu Hiiragi, and Haruhide Ishimaru

*Pharmaceutical Institute, Tohoku University, Aobayama, Sendai 980-8578, Japan


The new synthetic reaction of the 1-monosubstituted and 1,1-disubstituted 1,2,3,4-tetrahydroisoquinolines from 3-hydroxyphenethylamines and carbonyl compounds without an acidlc catalyst is described.

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Review | Regular issue | Vol 3, No. 4, 1975, pp. 343 - 361
Published online:
DOI: 10.3987/R-1975-04-0343
The Formation of Alkaloids in Mammalian Tissues

Arnold Brossi*

*The Department of Chemistry Research, Hoffman-La Roghe Inc., Nutley, New Jersey 07110, U.S.A.


Condensation of the amino acids L-dopa and L-tryptophan with acetaldehyde, a major metabolite of ethanol, may take place in mammalian systems. The following review summarizes the present knowledge on this interesting subject and includes the synthesis of a variety of substances which might be formed during such interactions.

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8 data found. 1 - 8 listed