Regular Issue

Vol. 16, No. 2, 1981

17 data found. 1 - 17 listed
Communication | Regular issue | Vol 16, No. 2, 1981, pp. 195 - 198
Published online:
DOI: 10.3987/R-1981-02-0195
Cyclizations of N-Alkylazinium Cations with Bisnucleophiles. One-step Route to Furo[2,3-b]quinoxalines

Valery N. Charushin, Oleg N. Chupakhin,* and Anatoly I. Rezvukhin

*Department of Organic Chemistry, Urals Polythcnical Institute, Sverdlovsk, 620002, Russia


N-Alkylquinoxalinium salts react with anions of β-diketones at a temperature below 20°C to yield endo-furo[2,3-b]quinoxalines.

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Communication | Regular issue | Vol 16, No. 2, 1981, pp. 199 - 202
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DOI: 10.3987/R-1981-02-0199
Synthesis and Acylation of 2-(2,5-Dihydro-1,3-thiazol-2-yl)-2-phenylhydrazonoacetic Acid Esters

Johann Gasteiger* and Ulrich Strauß

*Institut für Organische Chemie, Technische Universität München, Lichtenbergstrasse 4, D-85747 Garching, Germany


The preparation of 2-(2,5-dihydro-1,3-thiazol-2-yl)-2-phenylhydrazonoacetic acid esters is described. Acylation of these compounds occurs at the sulfur atom with concomitant opening of the dihydrothiazole ring to yield 3-(Z-2-acylthiovinylimino)-2-phenylhydrazono-butanoic acid esters.

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Communication | Regular issue | Vol 16, No. 2, 1981, pp. 203 - 207
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DOI: 10.3987/R-1981-02-0203
Simple Synthetic Route to “Oxa-Deaza-Flavins” (2H-[1]-Benzopyrano[2,3-d]pyrimidine-2,4(3H)-diones)

David J. Blythin,* Martin S. Domalski, Young C. Kim, James Kuo, and Jen-Her Liu

*Department of Chemical Research, Medicinal Pharmaceutical Research Division, Schering-Plough Corporation, Bloomfield, NJ 07003, U.S.A.


The preparation and reduction of substituted [1]-benzopyrano[2,3-d]pyrimidine-2,4(3H)-diones, “oxa-deaza-flavins”, (II), are described.

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Communication | Regular issue | Vol 16, No. 2, 1981, pp. 209 - 214
Published online:
DOI: 10.3987/R-1981-02-0209
Reactions of 4-Methylene-2-phenyl-2-oxazolin-5-ones with Sulfer Ylides

Otohiko Tsuge,* Michihiko Noguchi, and Hiroyuki Moriyama

*Research Institute of Industrial Science, Faculty of Engineering, Kyushu University, 6-1, Kasuga-koen, Kasuga 816-8580, Japan


The reaction of 2-phenyl-4-phenylmethylene-2-oxazolin-5-one with dimethyloxosulfonium methylide proceeded via a nucleophilic attack of the methylide on the carbonyl carbon in the oxazolinone with concurrent ring opening to give 1:1 adduct, dimethyloxosulfonium (2-benzamido)cinnamoylmethylide. On the other hand, dimethylsulfonium phenacylide reacted with 4-phenylmethylene-, 4-(p-acetoxyphenyl)methylene-, 4-styrylmethylene-, 4-(2-furyl)methylene-, 4-[3-(1-acetylindolyl)]methylene-, or 4-dimethylmethylene-2-phenyl-2-oxazolin-5-one to give two stereoisomeric spirocyclopropanes and/or γ-pyrone derivatives respectively, whose yields were dependent on the reaction conditions.

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Communication | Regular issue | Vol 16, No. 2, 1981, pp. 215 - 220
Published online:
DOI: 10.3987/R-1981-02-0215
A General Synthesis of 7,9-Dialkyladeninium Salts

Tozo Fujii,* Tohru Saito, Teruyo Sakuma, Masako Minami, and Isao Inoue

*Faculty of Pharmaceutical Scicences, Kanazawa University, 13-1 Takara-machi, Kanazawa 920-0934, Japan


Alkylations of N6-methoxy-9-methyladenine (I) and 9-alkyl-N6-benzyloxyadenines (II-IV) with MeI, EtI, and PhCH2Br in N,N-dimethylacetamide yielded the corresponding 7-alkylated derivatives (X, XIV-XVI), together with small amounts of the N6-alkylated isomers (V, VII-IX). Hydrogenolysis of the former compounds with hydrogen and Raney Ni produced 7,9-dialkyladenines (XI-XIII).

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Communication | Regular issue | Vol 16, No. 2, 1981, pp. 221 - 225
Published online:
DOI: 10.3987/R-1981-02-0221
The Structure of the Alkaloid Macarpine

Narao Takao, Miyoko Kamigauchi, Makiko Sugiura, Ichiya Ninomiya, Okiko Miyata, and Takeaki Naito*

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


The revised structure of the alkaloid macarpine (1c), which was isolated from both the plants and callus of Macleaya cordata, was proposed and unambiguously established by its total synthesis.

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Communication | Regular issue | Vol 16, No. 2, 1981, pp. 227 - 230
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DOI: 10.3987/R-1981-02-0227
Longikaurin C, D, E and F; New Antibacterial Diterpenoids from Rabdosia longituba

Tetsuro Fujita,* Yoshio Takeda, and Tetsuro Shingu

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


Four new diterpenoids, longikaurin C, D, E and F with antibacterial activity were isolated from the leaves of Rabdosia longituba and their structures were shown to be (3), (4), (5) and (6), respectively.

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Communication | Regular issue | Vol 16, No. 2, 1981, pp. 231 - 233
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DOI: 10.3987/R-1981-02-0231
Studies on Heterocyclic Compounds IV. Novel Diazotization Product of Ethyl 5-Aminofuran-2-carboxylate

Sheng-Chu Kuo,* Chun-Hsiung Wu, Chung-Chiee Wang, Akira Tanaka, and Chun-Chen Liao

*School of Pharmacy, China Medical College, Taichung 400, Taiwan, R.O.C.


Using ethyl 5-aminofuran-2-carboxylate as starting material for diazotization following standard method, instead of obtaining the usual diazonium salt, we isolated and characterized an unexpected dimeric product—diethyl 2’3’4’5’-tetrahydro-5,5’-dioxo[2,3’-bifuran]-2,2’(5H)-dicarboxylate.

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Communication | Regular issue | Vol 16, No. 2, 1981, pp. 235 - 238
Published online:
DOI: 10.3987/R-1981-02-0235
Some Novel Reactions of Benzoxazole Derivatives with Dimethyl Acetylenedicarboxylate II

Norio Kawahara,* Michihiko Katsuyama, Tsuneo Itoh, and Haruo Ogura

*Hokkaido College of Pharmacy, 7-1 Katsuraoka-cho, Otaru 047-02, Japan


2-Alkylbenzoxazole derivatives (1) reacted with dimethyl acetylenedicarboxylate (DMAD) in alcoholic solvents at room temperature to afford tricyclic compound (2), hydration product (3), solvent adduct (5) and ring-opened compounds (4 and 6). And the ring-opened compound (6) is a main product of photocycloaddition reaction of 1 with DMAD.

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Communication | Regular issue | Vol 16, No. 2, 1981, pp. 239 - 241
Published online:
DOI: 10.3987/R-1981-02-0239
A Two Synthon Approach to Δ15,17,19-Yohimbane Skeleton via a N5,N10-Methylenetetrahydrofolate Model. A Facile Route to β-Carboline Alkaloids

Hans Bieräugel, Henk C. Hiemstra, and Upendra K. Pandit*

*Laboratory of Organic Chemistry, Institute of Molecular Chemistry, University of Amsterdam, Nieuwe Achtergracht 129, 1018 WS Amsterdam, The Netherlands


2[2-(1,5,5-Trimethyl-3-tosylimidazolidinyl)]-2-(2-methoxycarbonylphenyl)-1,3-dithiane (N5,N10-methylenetetrahydrofolate model 10) reacts in an acid catalyzed reaction with tryptamine to form the pentacyclic skeleton of Δ15,17,19-yohimbane in one practical step.

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Communication | Regular issue | Vol 16, No. 2, 1981, pp. 243 - 246
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DOI: 10.3987/R-1981-02-0243
Synthesis of Novel 1-Oxadethia-2-oxocephems

Kapa Prasad,* Helmut Hamberger, Peter Stütz, and Gerhard Schulz

*Sandoz Forschungsinstitut, 1235 Wien, Brunnerstraße 59, Austria


Synthetic methods for the preparation of compounds 13, 14, and 15 are described utilising acetoxy azetidinone (4) as starting material.

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Communication | Regular issue | Vol 16, No. 2, 1981, pp. 247 - 249
Published online:
DOI: 10.3987/R-1981-02-0247
A Facile Route to (±)-Quebrachamine

Seiichi Takano,* Chikara Murakata, and Kunio Ogasawara

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


A facile route to (±)-quebrachamine (1), the parent base of the aspidosperma indole alkaloids, has been developed through halolactonization reaction.

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Report | Regular issue | Vol 16, No. 2, 1981, pp. 251 - 256
Published online:
DOI: 10.3987/R-1981-02-0251
Synthesis of Some Pyrrolo[3,4-b]quinoxaline 4,9-Dioxides

Makhluf J. Haddadin* and M. Adnan Atfah

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


The syntheses of a number of derivatives of the, hitherto, unknown pyrrolo[3,4-b]quinoxaline 4,9-dioxides are reported.

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Report | Regular issue | Vol 16, No. 2, 1981, pp. 257 - 259
Published online:
DOI: 10.3987/R-1981-02-0257
The Origin of the N-Formyl Group in Nature and the Biogenesis of Catharine and Catharinine

Natesan Murugesan* and Maurice Shamma

*Department of Chemistry, The Pennsylvania State University, University Park, Pennsylvania 16802, U.S.A.


The presence of an N-formyl group in an alkaloid often points to an in vivo Baeyer-Villiger oxidative rearrangement of an iminium precursor. Vinblastine (3) is thus shown to be the most likely progenitor for the accompanying alkaloids catharine (1) and catharinine (2) in Catharanthus spp.

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Report | Regular issue | Vol 16, No. 2, 1981, pp. 261 - 264
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DOI: 10.3987/R-1981-02-0261
Reactions of Harmaline and Its Derivatives. VII. Synthesis of 11-Methoxyindoloquinolizidines by Photochemical Cyclization of Enamine Interamediates

Atta-ur-Rahman* and Maryam Ghazala

*H. E. J. Postgraduate Institute of Chemistry, University of Karachi, Karachi-75270, Pakistan


Reactions of harmaline with benzyl halide and their ring substituted analogues affords enamine intermediates, photocyclization of which results in the formation of reserpine analogues in high yields. The procedure thus provides a synthetic approach to pharmacologically interesting substances from readily accessible precursors.

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Report | Regular issue | Vol 16, No. 2, 1981, pp. 265 - 266
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DOI: 10.3987/R-1981-02-0265
Semisynthetic β-Lactam Antibiotics. IV. Synthesis of a New α-Hydrazinobenzyl-6α-methoxypenicilin

Goffredo Bolis, Piero Bellani, and Mario Pinza*

*Laboratories for Biomedical Research, ISF, Trezzano s/N, Milan, Italy


Acylation of 6β-amino-6α-methoxypenicillanate (4b) with the α-methylenehydrazinoacid chloride (3b) afforded the new 6α-methoxy-6β-triazinonepenicillin (5).

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Review | Regular issue | Vol 16, No. 2, 1981, pp. 267 - 291
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DOI: 10.3987/R-1981-02-0267
Synthesis of 4-Substituted Indoles and Their Elaboration to the Ergot Alkaloids

Alan P. Kozikowski*

*Department of Chemistry, University of Pittsburgh, Parkman Avenue & University Drive, Pittsburgh, PA 15260 , U.S.A.


All of the synthetically important methods which have been developed for the preparation of 4-substituted indoles are reviewed. The use of these materials in the construction of the ergot alkaloids is discussed.

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17 data found. 1 - 17 listed