Regular Issue

Vol. 6, No. 5, 1977

7 data found. 1 - 7 listed
Communication | Regular issue | Vol 6, No. 5, 1977, pp. 525 - 528
Published online:
DOI: 10.3987/R-1977-05-0525
Studies on Pyrimidine Derivatives. IV. Synthesis of Hydroxymethylpyrimidines by Means of the Homolytic Hydroxymethylation

Takao Sakamoto, Kazuko Konno, Takayasu Ono, and Hiroshi Yamanaka*

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


2-Hydroxymethyl- and 4-hydroxymethyl-pyrimidines were synthesized in yield ranging from 28 to 93% by the reactions of some simple pyrimidine derivatives with the hydroxymethyl radical generated from methanol and ammonium peroxydisulfate.

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Communication | Regular issue | Vol 6, No. 5, 1977, pp. 529 - 533
Published online:
DOI: 10.3987/R-1977-05-0529
A Facile Synthesis of 1-(2-Tetrahydrofuryl)-5-fluorouracil (Ftorafur)

Tetsuji Kametani,* Kazuo Kigasawa, Mineharu Hiiragi, Kikuo Wakisaka, Osamu Kusama, Hideo Sugi, and Kumeo Kawasaki

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


1- (2-Tetrahydrofuryl)-5-fluorouracil (1), a potent anti-tumor agent, was conveniently synthesized by the the condensation of 5-fluorouracil (2) with various 2-alkoxy-2,3,4,5-tetrahydrofurans (3a-j), and the best yield of 1 by this method was obtained in the reaction of 2-t-butoxy analog (3h).

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Communication | Regular issue | Vol 6, No. 5, 1977, pp. 535 - 540
Published online:
DOI: 10.3987/R-1977-05-0535
Studies on the Reactivity of Isoquinoline and Related Compounds. IV. Addition Reaction of Active Methylene Compounds with Isoquinline

Takayuki Shiraishi and Hiroshi Yamanaka*

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


In connection with addition reaction of acetic anhydride to the isoquinoline nucleus, reaction of active methylene compounds with isoquinoline (I) in acetic anhydride was investigated. Thus, the N-acetyl-1,2-dihydroisoquinoline derivatives such as 1-acetonyl- (IV), 1-phenacyl-2-acetyl-1,2-dihydroisoquinoline (X), diethyl 2-acetyl-1,2-dihydro-1-isoquinolylmalonate (XII), and α-(2-acetyl-1,2-dihydro-1-isoquinolyl)phenylacetic acid (XIII) were obtained.

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Communication | Regular issue | Vol 6, No. 5, 1977, pp. 541 - 545
Published online:
DOI: 10.3987/R-1977-05-0541
Preparation and Some Reactions of o-Nitrosoaniline

Musa Z. Nazer, Makhluf J. Haddadin, Joanna P. Petridou, and Costas H. Issidorides*

*Department of Chemistry, American University of Beirut, Beirut, Lebanon


Treatment of o-nitrosoaniline with benzofuran-3(2H)-ones in base gives the corresponding 3-(o-hydroxyphenyl)quinoxaline 1-oxides in good yield. The reaction of o-nitrosoaniline with benzoin gives a mixture of the mono- and di-N-oxides of 2,3-diphenylquinoxaline. o-Nitrosoaniline reacts readily with benzaldehyde to give 1-hydroxy-2-phenylbenzimidazole.

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Report | Regular issue | Vol 6, No. 5, 1977, pp. 547 - 550
Published online:
DOI: 10.3987/R-1977-05-0547
Convenient Synthesis of Nicotinamide Derivatives

Takushi Kurihara* and Toshiko Uno

*Faculty of Pharmaceutical Science, Osaka University of Pharmaceutical Sciences, 4-20-1 Nasahara, Takatsuki, Osaka 569-1094, Japan


A one-step synthesis of 5-acetyl-4-ethoxycarbonyl-2-methylnicotinamide (IV) by the reaction of ethyl 3-ethoxymethylene-2,4-dioxovalerate (I) with β-aminocrotonamide (II) was described, and this was easily converted to nicotinamide derivatives (VI, VII, and VIII).

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Review | Regular issue | Vol 6, No. 5, 1977, pp. 551 - 582
Published online:
DOI: 10.3987/R-1977-05-0551
Lactonalkaloide aus Amaryllidaceen

Werner Döpke*

*Fachbereich Chemie, Humboldt-Universität Berlin, Hessische Strasse 1-2, D-10115 Berlin, Germany


In dem folgenden Artikel wird elne kurze Übersicht übsr die zur Zeit bekannten Lacton- Lactol- Alkaloide aus der Familie der Amaryllidaceen gegeben. Es werden die wich-tigsten Strukturableitungen von Basen, die nahe mit dem Clivonin verwandt sind abgehandelt. Schließlich werden die wichtigsten Fragmentierungen im Massenspektrometer sowie die mÜgliche Biosynthese diskutiert.

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Review | Regular issue | Vol 6, No. 5, 1977, pp. 583 - 675
Published online:
DOI: 10.3987/R-1977-05-0583
Rearrangementws of t-Amine Oxides

Shigeru Oae* and Kenji Ogino

*Department of Chemistry, University of Tsukuba, 1-1-1 Ten-nodai, Tsukuba-shi, Ibaraki, 305-8571, Japan


Heteroaromatic N-oxides and related tertiary amine oxides react with acylating agents and undergo various reactions depending upon the nature of the amine oxides, acylating agents,etc. These reactions are broadly divided into the following five basic types of reactions: 1) deoxygenative reduction, 2) rearrangement to ring carbon, 3) rearrangement to side chain carbon, 4) other heteroaromatic rearrangements, 5) rearrangements of open-chain N-oxides.
Each of these five representative reactions are illustrated by numerous examples, including many of our mechanistic investigations, hoping eventually to serve as nice guides to new synthetic inventions and innovations. The contents of this review are the following:
1. Introduction
2. Deoxygenative Reduction of N-oxides
3. Reactions with acylating agents : Rearrangements to heteroaromatic ring
4. Reactions with acylating agents : Rearrangements to alkyl side-chain
5. Other related rearrangements of heteroaromatic N-oxides
6. Reactions of non-heteroaromatic N-oxides with acylating agents : Aliphatic t-amine
oxides, nitrones and azoxybenzenes
7. Acknowledgement

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7 data found. 1 - 7 listed