Regular Issue

Vol. 31, No. 1, 1990

25 data found. 1 - 25 listed
Communication | Regular issue | Vol 31, No. 1, 1990, pp. 1 - 4
Published online:
DOI: 10.3987/COM-89-5141
A New Route to 1,2-Dithiole-3-thiones (Trithiones) by the Reaction of Enaminones with Carbon Disulfide

Yoshinori Tominaga,* Hajime Norisue, Chizuko Kamio, Toshiyuki Masunari, Yuji Miyashiro, and Akira Hosomi*

*Faculty of Pharmaceutical Sciences, Nagasaki University, 1-14, Bunkyo-machi, Nagasaki 852-8521, Japan


Enaminones reacted with carbon disulfide in the presence of sodium hydroxide to give the corresponding 1,2-dithiole-3-thiones (trithiones) in 30-82% yields.

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Communication | Regular issue | Vol 31, No. 1, 1990, pp. 5 - 8
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DOI: 10.3987/COM-89-5196
A Stereocontrolled Synthesis of the 16-Membered Ring Macrolide Aglycones, Niddanolide, Carbonolide B, and Platenonolide W1

Noriyuki Nakajima, Kouichi Uoto, and Osamu Yonemitsu*

*Faculty of Pharmaceutical Sciences, Hokkaido University, Sapporo 060, Japan


The aglycones of the 16-membered ring macrolide antibiotics, niddanolide, carbonolide B, and platenonolide W1, were synthesized via the Yamaguchi esterification of the C1-10 segment and the C11-C15 segment, prepared stereoselectively from n-glucosed, followed by an intramolecular Wittig-Horner type cyclization.

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Communication | Regular issue | Vol 31, No. 1, 1990, pp. 9 - 12
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DOI: 10.3987/COM-89-5202
New and Efficient Synthesis of 5,6,7,8-Tetrahydroindolizidines. Application to the Synthesis of Pharmacologically Relevant Chiral Aminoderivatives from L-Asparagine

Peter Gmeiner* and Holger Lerche

*Institut für Pharmazie und Lebensmittelchemie, Ludwig-Maximilins-Universität, Sophienstraße 10, 8000 München 2, Germany


A convenient and high yielding cyclization reaction of N-pyrrolylbutyl triflates is shown. The method is applied to afford the potential DA agonists 3, enantiomerically pure from L-aspargine.

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Communication | Regular issue | Vol 31, No. 1, 1990, pp. 13 - 16
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DOI: 10.3987/COM-89-5207
A New Synthetic Approach to (+)-Galantinic Acid, Degradation Product from the Peptide Antibiotic Galantin I, via 4-Amino-3-hydroxypyranose

Shinzo Kano,* Tsutomu Yokomatsu, and Shiroshi Shibuya

*Tokyo College of Pharmacy, 1432-1 Horinouchi, Hachioji, Tokyo 192-0392, Japan


5-Phenylthioxazolidin-2-ones, derived from L-serine, were subjected to photo-induced radical allylation to give the corresponding 4-substituted 4,5-trans-5-allyloxazolidin-2-ones. 4-Ethoxyethyl derivative (13c) was led to N-Boc galantinic acid methyl ester via N-Boc 4-amino-3-hydroxypyranose.

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Communication | Regular issue | Vol 31, No. 1, 1990, pp. 17 - 22
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DOI: 10.3987/COM-89-5210
A Convenient, One-Pot Azulene Synthesis from Cyclohepta[b]furan-2-ones and Vinyl Ether and Its Analogues. (II). Acetals as Reagent

Tetsuo Nozoe,* Hidetsugu Wakabayashi,* Sumio Ishikawa, Chi-Phi Wu, and Paw-Wang Yang*

*Department of Chemistry, Faculty of Science, Josai University, 1-1 Keyakidai, Sakado, Saitama 350-0295, Japan


Variously functionalized azulene derivatives were synthesized in one-pot and by the reaction of cyclohepta[b]furan-2-ones with acetals of several aldehydes and ketones on heating at 160-190 °C in neat or aprotic solvent.

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Communication | Regular issue | Vol 31, No. 1, 1990, pp. 23 - 26
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DOI: 10.3987/COM-89-5228
Synthesis of 1,2,3,4,5,6-Hexahydro-8-hydroxy-2,6-epithio-3-benzazocine

Mikio Hori,* Hiroyuki Ozeki, Tatsunori Iwamura, Hiroshi Shimizu, Tadashi Kataoka, and Noriyuki Iwata

*Department of Pharmacognosy, Gifu College of Pharmacy, 6-1 Mitahora-higashi 5-chome, Gifu 502-8585, Japan


In anticipation of diminishing narcotism of 1,2,3,4,5,6-hexahydro-8-hydroxy-2,6-methano-3-benzazocine opioids, the corresponding 2,6-epithio-3-benzazocines (2) have been synthesized by intramolecular cyclization of 1-(2-aminoethyl)-3,4-dihydro-1H-2-benzothiopyrans (9) with tert-butyl hypochlorite, and subsequent treatment of the 5-membered cyclic aminosulfonium slats (17) with NaOH.

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Communication | Regular issue | Vol 31, No. 1, 1990, pp. 27 - 30
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DOI: 10.3987/COM-89-5233
Studies on the Alkaloids from Aconitum barbetum var. hispidum Ledeb.

Aina Lao, Hongcheng Wang, Jun Uzawa, Yasuo Fujimoto,* and Makoto Kirisawa

*College of Pharmacy, Nihon University, 7-7-1 Narashinodai, Funabashi-shi, Chiba 274-8555, Japan


A new C18-diterpenoid alkaloid, hispaconitine (1) and four known alkaloids, tuguaconitine (2), delsoline (3), 14-acetyldelcosine (4) and delcosine (5), have been isolated from the roots of Aconitum berbetum var. hispidum Ledeb. The structure of hispaconitine (1) was determined by 2D-nmr spectroscopic analyses.

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Paper | Regular issue | Vol 31, No. 1, 1990, pp. 31 - 36
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DOI: 10.3987/COM-89-5027
Studies in Spiroheterocycles: Part XXII: Synthesis of Novel Fluorine Containing Spiro[3H-indole-3,5’-(5H)pyrano[2,3-d]pyrimidine]-6’-carbonitriles and Ethyl Carboxylates

Krishna C. Joshi,* Renuka Jain, and Saroj Nishith

*Department of Chemistry, University of Rajasthan, Jaipur 302 004, India


A number of novel fluorine containing spiro[3H-indole-3,5’-(5H)-pyrano[2,3-d]pyrimidine]-6’-carbonitriles and ethyl carboxylates have been synthesized by the Michael reaction of 3-dicyano- and carboethoxycyanomethylene-2-oxindole with phenylbarbituric acid. As the reaction offers two possibilities, the formation of the pereferred product has been discussed. Further, the spiro compounds have been subjected to acetylation and methylation.

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Paper | Regular issue | Vol 31, No. 1, 1990, pp. 37 - 45
Published online:
DOI: 10.3987/COM-89-5083
Synthesis of Methyl 4-(2,2-Dimethoxyethyl)-6-hydroxy-7-methoxyindole-2-carboxylate: A Potential Intermediate for the Synthesis of the Central and Right Parts of the Anticancer Antibiotic CC-1065

Luis Castedo, Carlos F. Marcos, María Ruiz, and Gabriel Tojo*

*Departamento de Química Orgánica, Facultad de Farmacia, Universidad de Santiago de Compostela, E-15706, Santiago de Compostela, Spain


We describe an efficient synthesis of methyl 4-(2,2-diemthoxyethyl)-6-hydroxy-7-methoxyindole-2-carboxylate (5), a key inermediate for the synthesis of the cetnral and right parts of the antitumor agent CC-1065 (1) and of the inhibitors of cyclic adenosine-3’,5’-monophosphate phosphodiesterase PDE-I (2) and PDE-II (3).

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Paper | Regular issue | Vol 31, No. 1, 1990, pp. 47 - 57
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DOI: 10.3987/COM-89-5095
Chemistry of Silyl Thioketones. Part 6. Synthesis of 5-Membered Silyl-heterocycles via 1,3-Dipolar Cycloaddition to Aryl Silyl Thioketones

Bianca F. Bonini, Gaetano Maccagnani,* Germana Mazzanti, Ghamel Abdel-Lateef Achmed Atwa, Paolo Zani, and Gaetano Barbaro

*Dipartimento di Chimica Organica "A Mangini", Università degli Studi di Bologna, Viale Risorgimento, 4, I-40136 Bologna , Italy


Aryl silyl thioketones react with 1,3-dipoles (nitriloxides, nitrilimine and nitrile ylide) to give regiospecifically silyl thiaheterocycles. These cycloadducts undergo desilylation leading either to ring fragmentation products or to the H-substituted heterocycles.

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Paper | Regular issue | Vol 31, No. 1, 1990, pp. 59 - 65
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DOI: 10.3987/COM-89-5105
Studies on Dipolar Cycloaddition Reactions. Synthesis of 3,4-Disubstituted 1-(2,4-Dichlorobenzamidoyl)azetidin-2-ones and Fused Δ2-Pyrazolines

Chandra Sekhar Sarma, Probin C. Gogoi, and Jibon C. S. Kataky*

*Regional Research Laboratory, Jorhat 785 006, Assam, India


From the dipolar cycloaddition reactions of ketenes and aniles 2, the new azetidinones 3 and 4 were isolated. In addition the reaction between the nitrilimine 6 and cyclic olefins 7 gave new fused Δ2-pyrazolines 8, 9 and 10. The chemical behaviour and spectral data of the new compounds were determined.

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Paper | Regular issue | Vol 31, No. 1, 1990, pp. 67 - 78
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DOI: 10.3987/COM-89-5125
Fluorinated Analogues of the Imidazole Insect Growth Regulator KK-42

César Arbonés, Francisco J. Sánchez, Maria-Pilar Marco, Francisco Camps, and Angel Messeguer*

*Departmenr of Biological Chemistry, C.I.D. (CSIC), J. Giroba 18. 08034-Barcelona, Spain


The preparation of compounds 1b, 1c and 1e, monofluoro and trifluoromethyl analogues of the imidazole KK-42 (1a) is reported. The synthetic sequence involves the formation of an imine between the appropriate fluoro aldehyde and benzylamine, followed by condensation with tosylmethyl isocyanide (TosMIC) in basic media. Each step has been thoroughly studied and the whole procedure has been optimized for the case of model imidazole 1a. It has been observed that when possible, the imine formation proceeds with a concomitant Z/E isomerization on the olefin moiety of the α,β-unsaturated system. Finally, data on the biological activity of the title compounds as ecdysone antagonists are also presented.

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Paper | Regular issue | Vol 31, No. 1, 1990, pp. 79 - 86
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DOI: 10.3987/COM-89-5126
Synthesis of an Aminopyrazolidines Substituted Quinolone Acid

Kyoung Soon Kim* and Patrick C. Ryan

*Cancer and Infectious Diseases Research, The Upjohn Company, Kalamazoo, Michigan 49001, U.S.A.


A synthesis of a new heterocycle, 2-methyl-4-(S)-Cbz-aminopyrazolidine (2), and the preparation of aminopyrazolidine substituted quinolone acid 1 are reported.

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Paper | Regular issue | Vol 31, No. 1, 1990, pp. 87 - 95
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DOI: 10.3987/COM-89-5127
Synthesis of an Aminoisoxazolidine Substituted Quinolone Acid

Kyoung Soon Kim*

*Cancer and Infectious Diseases Research, The Upjohn Company, Kalamazoo, Michigan 49001, U.S.A.


New heterocycle aminoisoxazolidine 7 and tetrafluorobenzoic acid are synthesized for the synthesis of a quinolone antibacterial agent. The synthesis of a chiral aminoisoxazolidines substituted quinolone acid, U-82662A, is described.

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Paper | Regular issue | Vol 31, No. 1, 1990, pp. 97 - 107
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DOI: 10.3987/COM-89-5149
Synthesis of New Heterocyclic Ring Systems: Indeno[2,1-b]benzo[g]indolizine and indeno[1’,2’:5,4]pyrrolo[2,1-a]phthalazine

Francesco Campagna,* Angelo Carotti, Giovanni Casini, and Maria Macripò

*Dipartimento Farmaco-Chimico, Università di Bari, Via Amendola 173, 70126 Bari, Italy


Some derivatives of the title heterocycles have been prepared by a "one step" synthesis from 2-hydroxy-2-acylmethylene-1,3-indandiones, tosyl chloride and isoquinoline or phthalazine. The synthesis of new indeno[2,1-b]indolizine derivatives performed by using pyridine as base is also reported.

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Paper | Regular issue | Vol 31, No. 1, 1990, pp. 109 - 114
Published online:
DOI: 10.3987/COM-89-5150
Synthesis of 2-t-Butyl-5-hydroxypyrimidine via Hydrolysis of 2-t-Butyl-5-halopyrimidines

Richard Garth Pews*

*Organic Chemicals and Polymers Laboratry, Central Research, The Dow Chemical Company, Midland, Michigan 48674, U.S.A.


The hydrolysis of 2-t-butyl-5-halopyrimidine (halogen = bromine or chlorine) with sodium methoxide in methanol yields 2-t-butyl-5-hydroxypyrimidine. The side reaction product, 2-t-butylpyrimidine, is substantially reduced, especially in the case of the bromo derivative, with catalytic amounts of elemental sulfur.

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Paper | Regular issue | Vol 31, No. 1, 1990, pp. 115 - 122
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DOI: 10.3987/COM-89-5154
On the Multiplicity of Carbenes Conjugated with Pyrrole and Furan Moieties: Molecular Orbital Calculation and Reaction of 2-(1-Methyl)pyrrolylmethylene and 2-Furylmethylene with cis- and trans-Stilbenes

Katsuhiro Saito,* Takahiro Ushida, Hiroshi Fushihara,Yoshiro Yamashita, Shoji Tanaka, and Kensuke Takahashi

*Department of Applied Chemistry, Nagoya Institute of Technology, Gokiso-cho, Showa-ku, Nagoya 466-8555, Japan


The reaction of 2-(1-methyl)pyrrolylmethylene and 2-furylmethylene with cis- and trans-stilbenes proceeded in a stereospecific manner to give the corresponding cyclopropane derivatives to show that the multiplicities of these carbenes are singlet. The molecular orbital calculation showed that these carbenes are triplet in their ground state and nucleophilic both in singlet and triplet states.

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Paper | Regular issue | Vol 31, No. 1, 1990, pp. 123 - 127
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DOI: 10.3987/COM-89-5184
Novel Synthetic Route to Pyridine-2(1H)-thiones: Unexpected Products of the Reaction of β-Phenethylidenemalononitriles with Arylmethylenecyanothioacetamides

Galal Eldin Hamza Elgemeie*

*Chemistry Department, Faculty of Science, Bani Suef, Egypt


A novel synthesis of 3-cyanopyridine-2(1H)-thione derivatives utilizing arylmethylenecyanothioacetamides and β-phenethylidenemalononitriles as starting componets is described.

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Paper | Regular issue | Vol 31, No. 1, 1990, pp. 129 - 137
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DOI: 10.3987/COM-89-5194
A Novel One Pot Synthesis of 1,3,7-Triaryl-1,2,3,4-tetrahydro-4-oxo-5-phenyl-2-thioxo-5H-pyrano[2,3-d]pyrimidines

Vinod Kumar Ahluwalia,* Rachna Aggarwal, Mohammad Alauddin, Gurpreet Gill, and Chandra Has Khanduri

*Department of Chemistry, University of Delhi, Delhi-110 007, India


A novel one pot synthesis of 1,3,7-triaryl-1,2,3,4-tetrahydro-4-oxo-5-phenyl-2-thioxo-5H-pyrano[2,3-d]pyrimidines has been described. It utilizes the reaction of different thiobarbituric acids with chalcones.

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Paper | Regular issue | Vol 31, No. 1, 1990, pp. 139 - 147
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DOI: 10.3987/COM-89-5208
Unexpected Reaction between DCC and Cephalosporanic Acid Sulphones

Marco Alpegiani, Pierluigi Gissolino, Emanuele Arlandini, Daniela Borghi, and Ettore Perrone

*Farmitalia Carlo Erba, R&D, Infectious Diseases Dep., Via dei Gracchi 35, 20146 Milano, Italy


Cephalosporanic acid sulphones react with DCC to give a novel 4-spiroazetidinyl-Δ2-cephem structure with high stereoselectivity. The reaction, though general for cephem-4-carboxylic acids, is deeply affected by oxidation at sulphur; an external base was required for the 1-sulphide 3, and stereoselectivity was lost with the 1α-sulphoxide 9.

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Paper | Regular issue | Vol 31, No. 1, 1990, pp. 149 - 152
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DOI: 10.3987/COM-89-5209
Labrandine: A New Pentacyclic Proaporphine Alkaloid from Roemeria hybrida

Belkis Gözler*

*Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Ege University, Izmir, Turkey


The pentacyclic phenolic proaporphine (-)-labrandine (1) has been isolated from Turkish Roemeria hybrida (L.) DC. (Papaveraceae). O-Methylation furnished (-)-misramine (2) which is also present in the plant. Acetylation of 1 afforded (-)-2,10-deacetyllabrandine (3), and selective deacetylation of the latter provided (-)-10-acetyllabrandine (4).

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Paper | Regular issue | Vol 31, No. 1, 1990, pp. 153 - 161
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DOI: 10.3987/COM-89-5222
Pollycyclic N-Hetero Compounds. XXXI. Synthesis and Anti-platelet Aggregation Activity of 4-Substituted 5,6-Dihydrobenzo[h]quinazolines

Takashi Hirota,* Kenji Sasaki, Hiromi Ohtomo, Ayako Uehara, and Taiji Nakayama

*Faculty of Pharmaceutical Sciences, Okayama University, 1-1-1 Tsushima-naka, Okayama 700-8530, Japan


4-Substituted 5,6-dihydrobenzo[h]quinazolines (IV) were synthesized by the reaction of 4-chloro-5,6-dihydrobenzo[h]quinazoline (II) with amines (III) and their inhibitory activity against platelet aggregation was investigated.

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Paper | Regular issue | Vol 31, No. 1, 1990, pp. 163 - 172
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DOI: 10.3987/COM-89-5231
Synthesis and Characterization of [8](3,6)Azepinophane and [8](3,6)Oxepinophanes

Kyosuke Satake,* Isao Umemoto, Kunihiro Usumoto, Masaru Kimura, Shiro Morosawa, Tsutomu Kumagai, and Toshio Mukai

*Department of Chemistry, Faculty of Science, Okayama University, 3-1-1 Tsushima-naka, Okayama 700-8530, Japan


[8](3,6)Azepinophane (methyl 3,6-octano-1H-azepine-4-carboxylate) and [8](3,6)oxepinophane (3,6-octanoxepin) were synthesized from bicyclo[8.2.2]undecadiene, and structural features of them were also studied on the basis of their spectral data. The effect of the substituents at 3 and 6 positions on the structure of 1H-azepine ring was elucidated by comparison of several 3,6-dialkyl-1H-azepine derivatives with the title azepinophane.

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Paper | Regular issue | Vol 31, No. 1, 1990, pp. 173 - 186
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DOI: 10.3987/COM-89-5240
Synthesis and Reactivity of 2-(1,3-Dithian-2-yl)indoles. III. Influence of the Indole Protective N-Phenylsulfonyl Group

Mario Rubiralta,* Anna Diez, Ignashi Reig, Josep Castells, Jean-Luc Bettiol, David S. Grierson, and Henri-Philippe Husson

*Laboratory of Organic Chemistry, Faculty of Pharmacy, University of Barcelona, Av. de Joan XXIII, s/n, 08028 Barcelona, Spain


Formation of the anion 2-(1,3-dithian-2-yl)indoles was shown to be possible when the indole nitrogen is protected by a p-methoxyphenylsulfonyl group. In contrast to the corresponding N-phenylsulfonylindole dithiane 1, the anion of dithiane 2 reacts efficiently with electrophiles. The influence of the indole protective group on the metallation of 2-bis(ethylthio)methyl-1-(phenylsulfonyl)indole (14) and the corresponding sulfoxide 24 with n-butyllithium is also reported.

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Paper | Regular issue | Vol 31, No. 1, 1990, pp. 187 - 190
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DOI: 10.3987/COM-89-5267
Bakuchicin, A New Simple Furanocoumarin from Psoralea corylifolia L.

Yoshikazu Kondo,* Atsushi Kato, Yoshiyuki Kubota, and Shigeo Nozoe

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


A new simple furanocoumarine, bacuchicin, has been isolated from the hexane-extract of seeds of Psoralea corylifolia L. (Leguminosae) alone with stigmasterol, psoralen and bakuchiol. The structure of bakuchicin has been shown as 8-oxo-8H-furo[2,3-f][1]benzopyran (1) by spectral means.

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25 data found. 1 - 25 listed