Regular Issue

Vol. 12, No. 7, 1970

13 data found. 1 - 13 listed
Communication | Regular issue | Vol 12, No. 7, , pp. 893 - 896
Published online:
DOI: 10.3987/R-1979-07-0893
Biomimetic Synthesis of Protoberberine Alkaloids and Aporphine Alkaloids through N-Oxide Intermediates

Tetsuji Kametani* and Masataka Ihara

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


Reaction of (±)-reticuline N-oxide (3) with cuprous chloride in methanol, followed by treatment with sodium hydrosulphite, gave (±)-corytuberine (8) in excellent yield, while phenol oxidative coupling of (±)-orientaline N-oxide (4) was less effective under the same conditions. Treatment of 3 with ferrous sulphate in methanol afforded (±)-coreximine (5) and (±)-scoulerine (6), but formation of the protoberberine (7) from 4 with this reagent required acidic conditions.

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Communication | Regular issue | Vol 12, No. 7, , pp. 897 - 902
Published online:
DOI: 10.3987/R-1979-07-0897
Syn Selectivity in the Reactions of Azomethiene Imines and Azomethine Oxides with cis-3,4-Disubstituted Cyclobutenes

Remo Gandolfi,* Missimo Ratti, Lucio Toma, and Carlo De Micheli

*Dipartamento di Chimica Organica, Università di Pavia, V. le Taramelli 10, 27100 Pavia, Italy


3,4-Dihydroisoquinoline-N-phenylimine reacted with cis-3,4-dichloro, -dihydroxy and -diacetoxycyclobutenes to give the sterically disfavoured syn adducts as dominant products; with carbonyldioxy and dicarbomethoxycyclobutenes repulsive steric interactions led to the prevailence of the anti adducts. An increased syn selectivity was found for the reactions of 3,4-dihydroisoquinoline-N-oxide with diacetoxycyclobutene and of nitro substituted 3,4-dihydroisoquinoline-N-phenylimines with dichlorocyclobutene.

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Communication | Regular issue | Vol 12, No. 7, , pp. 903 - 907
Published online:
DOI: 10.3987/R-1979-07-0903
Synthesis of 1,6-Diazaphenalene, a Vinylogous Imidazole

Jen-C. Chang, Mustafa I. El-Sheikh, and James M. Cook*

*Department of Chemistry, University of Wisconsin-Milwaukee, Milwaukee, Wisconsin 53201, U.S.A.


The simple synthesis of a new heterocycle,1,6-diazaphenalene (2), a vinylogous imidazole is described; the key step in the synthesis was conversion of 7 to 8 by cleavage of the N-O bond followed by hydrogen shifts under modified Semmler Wolff conditions [CF3COOH, (CF3CO)2O, HCl].

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Communication | Regular issue | Vol 12, No. 7, , pp. 909 - 912
Published online:
DOI: 10.3987/R-1979-07-0909
Synthesis of Spirofluorenes via Ketene Adducts

Magid A. Abou-Gharbia and Madeleine M. Joullié*

*Department of Chemistry, University of Pennsylvania, 231 South 34th Street Philadelphia, PA 19104-6323, U.S.A.


New classes of spirofluorenes were prepared via simple transformations of ketene adducts.

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Communication | Regular issue | Vol 12, No. 7, , pp. 913 - 916
Published online:
DOI: 10.3987/R-1979-07-0913
Synthesis of 1-Benzazocin-5-one Derivatives from a 1,2,3,4-Tetrahydrocyclopent[b]indole; a Synthetic Approach to Mitomycins

Tetsuji Kametani,* Tatsushi Ohsawa, and Masataka Ihara

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


Photo-oxygenation of 4-benzyl-1,2,3,4-tetrahydro-5,7-dimethoxy-6-methylcyclopent[b]indole (14), derived from 2,4-dimethoxy-3-methylacetanilide (6) in eight steps, gave, in excellent yield, 1-benzyl-1,2,3,4,5,6-hexahydro-2,5-diketo-8,10-dimethoxy-9-methyl-1-benzazocine (15), which was converted to 1-benzyl-1,2,3,4,5,6-hexahydro-2-keto-5,5,8,10-tetramethoxy-9-methyl-6-methylene-1-benzazocine (19).

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Communication | Regular issue | Vol 12, No. 7, , pp. 917 - 920
Published online:
DOI: 10.3987/R-1979-07-0917
Thermal Decomposition of 2H-[1,2,4]Oxadiazolo[2,3-a]pyridine-2-thione and 2H-[1,2,4]Oxadiazolo[2,3-b]pyridazine-2-thione

Akio Ohsawa, Heihachiro Arai, and Hiroshi Igeta*

*School of Pharmaceutical Sciences, Showa University, 1-5-8 Hatanodai, Shinagawa-ku, Tokyo 142-8555, Japan


Pyrolysis of 2H-[1,2,4]oxadiazolo[2,3-a]pyridine-2-thione gave 3-(2-pyridyl)-2H-pyrido[1,2-a]-s-triazine-2,4(3H)-dione. 2-Isocyanatopyridine which is considered to be the intermediate in the reaction was utilized to the synthesis of N,N’-substituted ureas. Similar investigation was carried out on 2H-[1,2,4]oxadiazolo[2,3-b]pyridazine-2-thione.

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Communication | Regular issue | Vol 12, No. 7, , pp. 921 - 924
Published online:
DOI: 10.3987/R-1979-07-0921
The Synthesis of Benzolactones by Palladium Catalyzed Carbonylation

Miwako Mori, Katsumi Chiba, Nobuo Inotsume, and Yoshio Ban*

*Faculty of Pharmaceutical Sciences, Hokkaido University, Kita 12 Nishi 6, Kita-ku, Sapporo, Hokkaido 060-0812, Japan


Phthalide was easily prepared from o-bromobenzyl alcohol in the presence of a catalytic amount of Pd(OAC)2 and PPh3 under an atmospheric pressure of carbon monoxide in a good yield. When a large amount of PPh3 was used as a ligand, a better result was obtained. The six- and seven-membered benzolactones were synthesized by the same procedure.

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Communication | Regular issue | Vol 12, No. 7, , pp. 925 - 928
Published online:
DOI: 10.3987/R-1979-07-0925
Synthesis of Benzo[g]indolizines. Reaction of Acid Anhydrides with Isoquinolinium Methylides

Tetsuzo Kato,* Takuo Chiba, and Toshiki Sasaki

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


Reaction of isoquinolinium bis(ethoxycarbonyl)methylide (1) with acid anhydrides, such as acetic anhydride, propionic anhydride, n-butyric anhydride, and phenylacetic anhydride, gives rise to the benzo[g]indolizines, ethyl 2-acyloxypyrrolo[2,1-a]isoquinoline-3-carboxylate (where acyl is acetyl (5), propionyl (6), n-butyryl (7), and phenylacetyl (8), respectively). Similar reaction of isoquinolinium cyano(ethoxycarbonyl)methylide (2) affords the same products (5, 6, 7, and 8).

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Report | Regular issue | Vol 12, No. 7, , pp. 929 - 931
Published online:
DOI: 10.3987/R-1979-07-0929
The Identity of Glycophymine and Glycosminie: An Alkaloid of Glycosmis arborea (Roxb.) DC

J. Bhattacharyya* and S. C. Pakrashi

*Department of Chemistry and Geology, Clemson University, Clemson, SC 29631, U.S.A.


Glycophymine, a new alkaloid reported from Glycosmis pentaphylla is shown to be identical to glycosminine isolated from the same plant earlier.

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Report | Regular issue | Vol 12, No. 7, , pp. 933 - 942
Published online:
DOI: 10.3987/R-1979-07-0933
Synthesis of Seco-Mitosane Type Compounds as Key Intermediates to Mitomycins

Tetsuji Kametani,* Kimio Takahashi, Masataka Ihara, and Keiichiro Fukumoto

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


1,3,4,6-tetrahydro-6-methylene-1-benzazocin-5(2H)-ones (4 and 13) were prepared from 1,3,4,6-tetrahydro-1-benzazocin-5(2H)-ones (3 and 12) by treatment with N,N,N’,N’-tetramethyldiaminomethane and acetic anhydride. Functionallisation of the methylene groups of (4 and 13) and transannular cyclisation of the seco-mitosane type compounds (16 and 17) are also described.

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Report | Regular issue | Vol 12, No. 7, , pp. 943 - 946
Published online:
DOI: 10.3987/R-1979-07-0943
Kuwanon F, a New Flavanone Derivative from the Root Bark of the Cultivated Mulberry Tree (Morus alba L.)

Taro Nomura* and Toshio Fukai

*School of Pharmaceutical Sciences, Toho University, 2-2-1, Miyama, Funabashi, Chiba 274-8510, Japan


A new flavanone derivative containing 2-methyl-2-(4-methylpent-3-enyl)chromene ring named kuwanon F was isolated from the root bark of the cultivated mulberry tree (a variety of Morus alba L.). The structure was shown to be I on the basis of spectral and chemical data.

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Report | Regular issue | Vol 12, No. 7, , pp. 947 - 948
Published online:
DOI: 10.3987/R-1979-07-0947
Synthesis of (±)-Oxadethia-2,3-benzocephems

Masayuki Shibuya* and Seiju Kubota

*Faculty of Pharmaceutical Sciences, University of Tokushima, Sho-machi 1, Tokushima 770-8505, Japan


The new 1-oxadethia-2,3-benzocephem ring system has been obtained by a one step synthesis from the readily available 4-acetoxyazetidin-2-one (2).

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Review | Regular issue | Vol 12, No. 7, , pp. 949 - 975
Published online:
DOI: 10.3987/R-1979-07-0949
Synthesis of Nitrogen-containing Heterocycles by the Imino Diels-Alder Reaction

Steven M. Weinreb* and Jeremy I. Levin

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


This review describes the major advances reported during the past fifteen years on synthesis of heterocyclic compounds using imino dienophiles in the Diels Alder [4+2]-cycloaddition reaction.

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13 data found. 1 - 13 listed