Regular Issue

Vol. 3, No. 8, 1975

6 data found. 1 - 6 listed
Communication | Regular issue | Vol 3, No. 8, 1975, pp. 615 - 618
Published online:
DOI: 10.3987/R-1975-08-0615
Indolizine Derivatives. IV. Evidence for a Disproportnation Dehydrogenation Mechanism in the Perkin Reaction of 2-Pyridinecarbaldehyde in the Presence of α,β-Unsaturated Carbonyl Compounds to Give 1-Acylpyrrolo[2,1,5-cd]indolizines

Esko Pohjala*

*Department of Chemistry, Technical University of Helsinki, P.O. Box 6100, FIN-02150 HUT Espoo, Finland


In the Perkin reaction of 2-pyridinecarbaldehyde (1) with 3-buten-2-one (2) and Ac2O/KOAc the normal Perkin reaction product, acetic 3-(2-pyridyl)acrylic anhydride (3), disproportionates. The reduction products include 3-indolizinyl acetate (4), which with 2 cyclizes to 1-(1,2-dihydro-1-pyrrolo[2,1,5-cd]ndolizinyl)ethanone (5). Dehydrogenation of 5 then affords 1-(1-pyrrolo[2,1,5-cd]indolizinyl)ethanone (6).

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Communication | Regular issue | Vol 3, No. 8, 1975, pp. 619 - 626
Published online:
DOI: 10.3987/R-1975-08-0619
Novel Formation of the Benzimidazo[2,1-a]isoquinoline and Benz[c]acridine from the 1,2,3,4-Tetrahydro-1-(2-nitrophenethyl)-isoquinoline with Triethyl Phosphite

Tetsuji Kametani,* Yasuo Fujimoto, and Masakatsu Mizushima

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


Reductive cyclisation of 1,2,3,4-tetrahydro-6,7-dimethoxy-1-(4,5-dimethoxy-2-nitrophenethyl)isoquinoline (10) and its 2-methyl derivative (11) with triethyl phosphite gave 5,6-dihydro-2,3,9,10-tetramethoxybenzimidazo[2,1-a]isoquinoline (13) and 2,3,9,10- tetramethoxybenz[c]acridine (18), respectively.

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Communication | Regular issue | Vol 3, No. 8, 1975, pp. 627 - 631
Published online:
DOI: 10.3987/R-1975-08-0627
A Total Synthesis of Angustine

Tetsuji Kametani,* Mitsuhiro Takeshita, Masataka Ihara, and Keiichiro Fukumoto

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


A total synthesis of angustine (1) was accomplished via condensation of tryptamine with the lactone (5) which was prepared from 4-methyl-5-vinylnicotinonitrile (4), followed by cyclisation of the 7-azacarbostyril (8). Gentianine (6) was also synthesised by two routes from the nicotinonitrile (4).

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Communication | Regular issue | Vol 3, No. 8, 1975, pp. 633 - 637
Published online:
DOI: 10.3987/R-1975-08-0633
Reaction of m-Nitrobenzylideneacetylacetone with Phenyl- and Methylhydrazines

Takushi Kurihara,* Toshiko Sakaguchi, and Hiroshi Hirano

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


Reaction of m-nitrobenzylideneacetylacetone with phenyl- and methylhydrazine in aqueous acetonitrile, methanol, and glacial acetic acid afforded 4-(α-hydroxy-, methoxy-, and acetoxy-m-nitrobenzyl)-3,5-dimethyl-1-phenylpyrazoles (Va-VIIa) and the corresponding 1-methyl derivatives (Vb-VIIb), presumably via the pseudo-bases (III), in excellent yields.

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Communication | Regular issue | Vol 3, No. 8, 1975, pp. 639 - 649
Published online:
DOI: 10.3987/R-1975-08-0639
Studies on the Synthesis of Bisindole Alkaloids. II. The Synthesis of 3’,4’-Dehydrovinblastine, 4’-Deoxovinblastine and Related Analogues. The Biogenetic Approach

James P. Kutney,* Arnold H. Ratcliffe, Adi M. Treasurywala, and Stephen Wunderly

*Department of Chemisry, University of British Columbia, Vancouver 8, V5T 1W5, Canada


A novel approach to the synthesis of bisindole alkaloids in the vinblastine series has been developed. This approach, which originates from biogenetic considerations is exemplified by the coupling of catharanthine and dihydrocatharanthine N-oxides with vindoline under Polonovski-type fragmentation conditions. The method which provides dimers with natural stereochemistry at C18, represents an exciting entry into this complex family from two readily available alkaloids.

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Review | Regular issue | Vol 3, No. 8, 1975, pp. 651 - 690
Published online:
DOI: 10.3987/R-1975-08-0651

Kenneth L. Stuart*

*Department of Chemsitry, University of the West Indies, Mona, Kingston 7, Jamaica


The Chemistry and uses of furazans (1,2,5-oxadiazoles) and furoxans (furazan-2-oxides) are reviewed.

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6 data found. 1 - 6 listed