Regular Issue

Vol. 26, No. 12, 1987

34 data found. 1 - 30 listed Next Last
Communication | Regular issue | Vol 26, No. 12, 1987, pp. 3051 - 3054
Published online:
DOI: 10.3987/R-1987-12-3051
Synthesis of Optically Active Hetero Alkylaryl Alcohols by Baker‘s Yeast

Mitsuhiro Takeshita, Katsuya Terada, Nami Akutsu, Sachiko Yoshida, and Takumi Sato

*Tohoku Pharmaceutical University, 4-4-1 Komatsushima, Aoba-ku, Sendai 981-8558, Japan


Synthesis of optically active hetero alkylaryl alcohols have been examined using baker’s yeast

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Communication | Regular issue | Vol 26, No. 12, 1987, pp. 3055 - 3058
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DOI: 10.3987/R-1987-12-3055
Corialstonine, a Novel Quinoline Alkaloid from Alstonia coriacea

Abdallah Cherif, Georges Massiot, and Louisette Le Men-Olivier

*Laboratorie de Pharmacognosie, Facluté de Pharmacie, U.A. n°492 au C.N.R.S., 51, rue Cognacq-Jay, F-51096 Reims Cedex, France


Corialstonine is a novel quinoline alkaloid isolated from Atstonia coriacea. Its structure illustrates a possible new transformation of indales into quinolines.

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Communication | Regular issue | Vol 26, No. 12, 1987, pp. 3059 - 3063
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DOI: 10.3987/R-1987-12-3059
Synthesis of 5,6,9,10,11,11a-Hexahydro-8H-naphtho[2,1-a]quinolizine

María Fernández Fernández and Mónica M. Söllhuber

*Departamento de Química Orgánica y Farmacéutica, Facultad de Farmacia, Universidad Complutense de Madrid, Ciudad Universitaria, 28040 Madrid, Spain


Naphtho[2,1-a]quinolizidine was synthesized by the reaction of 1,2- dihydrobenz[f]isoquinoline with methyl vinyl ketone. The heterolytic fragmentation of l0-p-tosyl-5,6,9,10,11,11a-hexahydro-8H-naphtho[2,1-a]quinolizine(11) is described.

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Communication | Regular issue | Vol 26, No. 12, 1987, pp. 3065 - 3069
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DOI: 10.3987/R-1987-12-3065
A New Access to 2-Benzoylquinoline and 1-Benzoylisoquonoline Using a Novel Mode of Base-induces Decomposition of N-Alkoxypyridinium Salts

Henri Sliwa and Lassina Outtara

*Laboratoire de Chimie Organique et Environnement, Université des Sciences et Technologies de Lille, Bat. C4 -2eme Etage, 59655 Villeneuve d‘ Ascq Cedex, France


A novel mode of fragmentation alkoxylogous of Katritzky’s mode A of decomposition of N-alkoxypyridinium salts can become exclusive in the quinoline and isoquinoline series, providing a new access to benzoyl derivatives of these hrterocycles.

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Communication | Regular issue | Vol 26, No. 12, 1987, pp. 3071 - 3075
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DOI: 10.3987/R-1987-12-3071
Reversible Formation of a Pseudobase from 1-Methylpyridinium-3-carb(ox)aldehyde

James F. Rusling and Petr Zuman

*Department of Chemistry, University of Connecticut, Storrs, CT 06269-3060, U.S.A.


The geminal diol anion of 1-methylpyridinium-3-carb(ox)aldehyde hydrate in aqueous alkaline solutions forms an unstable pseudobase by nucleophilic attack of hydroxide ion at the pyridinium ring. This reaction with pKa - 14.4 is unique among 1-methylpyridiniumcarboxaldehydes for the 3-isomer.

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Communication | Regular issue | Vol 26, No. 12, 1987, pp. 3077 - 3079
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DOI: 10.3987/R-1987-12-3077
New Route to Phthalideisoquinoline Alkaloids: Synthesis of (±)-Cordrastine I and II

Kazuhiko Orito, Hiroshi Suginome, S. Osmund De Silva, and Russel Rodrigo

*Division of Molecular Chemistry, Graduate School of Engineering, Hokkaido University, Kita 13 Nishi 8, Kita-ku, Sapporo, Hokkaido 060-0828, Japan


Acid-catalyzed isomerization of the keto-lactone (3) provided the immonium salt (6), sodium borohydride reduction of which gave (±)-cordrastine I (7) and II (8) after acid treatment.

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Communication | Regular issue | Vol 26, No. 12, 1987, pp. 3081 - 3083
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DOI: 10.3987/R-1987-12-3081
Intramolecular Cyclizations of Hantzsch 1,4-Dihydropyridines: Synthesis of Di- and Tetrahydroindeno[2,1-c]pyridines

Steven D. Young, Stella W. King, and David C. Remy

*Department of Medicinal Chemistry, Merck Sharp and Dohme Research Laboratories, West Point, PA 19486, U.S.A.


Hantzsch 4-phenyl-1,4-dihydropyridines bearing electrophilic ortho substituents react with trimethylsilyl cyanide/zinc iodide or base resulting in an intramolecular cyclization reaction to give di-and tetrahydroindeno[2,1-c]pyridines in good yield.

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Communication | Regular issue | Vol 26, No. 12, 1987, pp. 3085 - 3088
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DOI: 10.3987/R-1987-12-3085
Syntheses of 1,4-Oxazepines, 1,4-Diazepines, and Their 5-Oxo Derivatives from 2-Pyridones

Jyoji Kurita, Takeharu Yoneda, Naoki Kakusawa, and Takashi Tsuchiya

*School of Pharmacy, Hokuriku University, 3-Ho, Kanagawa machi, Kanazawa 920-1181, Japan


Thermolysis of the 3-aza-7-oxa- (11) and 3,7-diaza-4-oxotricyclo[,5]heptanes (12), prepared from 2-pyridones via four steps, resulted in valence isomerization with ring opening to give the novel 1,4-oxazepin-5-ones (14) and 1,4-diazepin-5-ones N (15), respectively, which were treated with triethyloxonium tetrafluoroborate to afford the fully unsaturated 1,4-oxazepines (16) and 1,4-diazepines (17), respectively.

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Communication | Regular issue | Vol 26, No. 12, 1987, pp. 3089 - 3092
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DOI: 10.3987/R-1987-12-3089
Electrophilic ipso-Substitution of 5-Bromouridines with Diaryl Disulfides. Novel Synthesis of 5-Arylthiouridines

Kosaku Hirota, Tetsuo Tomishi, and Yoshifumi Maki

*Labolatory of Medicinal Chemistry, Gifu Pharmaceutical University, 6-1 Mitahora-higashi 5-chome, Gifu 502-8585, Japan


Reaction of 5-bromo-2’,3’-O-isopropylideneuridine (1) with diaryl disulfides in the presence of base induced an electrophilic ispo-substitution to give 5-arylthiouridine derivatives (2).

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Communication | Regular issue | Vol 26, No. 12, 1987, pp. 3093 - 3096
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DOI: 10.3987/R-1987-12-3093
A New Route to Quassin Basic Skeleton via Allenecarboxylate Intramolecular Cycloaddition

Mitsutaka Yoshida and Ken Kanematsu

*Institute of Synthetic Organic Chemistry, Faculty of Pharmaceutical Sciences, Kyushu University, 3-1-1 Maidashi, Higashi-ku, Fukuoka 812-8582, Japan


The new route to quassin basic skeleton, tetracyclic lactones has been realized via the intramolecular Diels-Alder reaction of allene-1,3-dicarboxylates.

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Communication | Regular issue | Vol 26, No. 12, 1987, pp. 3097 - 3100
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DOI: 10.3987/R-1987-12-3097
Reduction of 3,4-Disubstituted 1,6-Propano-1H,6H-3a-thia(SIV)-1,3,4,6-tetraazapentalene-2,5(3H,4H)-dithione with Sodium Borohydride

Noboru Matsumura, Masaaki Tomura, Osamu Mori, Masataka Ukawa, and Shigeo Yoneda

*Department of Applied Chemistry, College of Engineering, University of Osaka Prefecture, Sakai, Osaka 593-8531, Japan


Reduction of tetraazapentalene derivatives with sodium borohydride (NaBH4) afforded the ring-opening compound, 1,3-bis(substituted thiocarbamoyl)perhydropyrimidine, in goad yields by the reduction-elimination of the C=SIV moiety.

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Communication | Regular issue | Vol 26, No. 12, 1987, pp. 3101 - 3104
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DOI: 10.3987/R-1987-12-3101
Synthesis of 1-(2-Pyridyl)indoles by the Photoreaction of 2-Fluoropyridine with Indoles

Koh-ichi Seki, Kazue Ohkura, Masanao Terashima, and Yuichi Kanaoka

*Faculty of Pharmaceutical Scicences, Higashinihonngakuen University, 1757 Kanazawa, Toubetu-cho, Ishikari-gun, Hokkaodo 061-0212, Japan


Photoreaction of 2-fluoropyridine with indoles gave 1-(2-pyridyl)indoles regioselectively. The yields of the coupling products improved significantly by using the indole anion derivatives instead of the indoles.

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Communication | Regular issue | Vol 26, No. 12, 1987, pp. 3105 - 3109
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DOI: 10.3987/R-1987-12-3105
Synthesis and Properties of Norcaradiene-Cycloheptatriene System Fused with Isoxazole Ring

Nobuhiro Kanomata, Makoto Nitta, Kensuke Takahashi, Yutaka Takakura, and Katsuhiro Saito

*Department of Chemistry, School of Science and Engineering, Waseda University, 3-4-1 Okubo, Shinjuku-ku, Tokyo 169-8555, Japan


Novel norcaradiene-cycloheptatriene systems fused with arylisoxazoles were synthesized and their temperature dependent 1H nmr spectra were studied. while the fusion of isoxazole ring much shifted the norcaradiene-cycloheptatriene equilibrium to the side of norcaradiene form, the rapid isomerizations of the norcaradienes with their enantiomers were observed and their δG‡c values were obtained.

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Communication | Regular issue | Vol 26, No. 12, 1987, pp. 3111 - 3114
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DOI: 10.3987/R-1987-12-3111
Studies of as-Triazine Derivatives. X. Addition Reaction of Phenylmagnesium Bromide with 1,2,4-Triazines

Shoetsu Konno, Mataichi Sagi, Nobuko Yoshida, and Hiroshi Yamanaka

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


The reaction of 1,2,4-triazine with phenylmagnesium bromide was investigated. Every position of 3, 5, and 6 in a 1,2,4-triazine ring is active in the addition reaction of Grignard reagents. Since 5-phenyl-1,2,4-triazine, 5,6-diphenyl-1,2,4-triazine, and 3,5,6-triaryl-1,2,4-triazine were obtained subsequently, it was comfirmed that the most active position was position 5 and the least active one was position 3.

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Paper | Regular issue | Vol 26, No. 12, 1987, pp. 3115 - 3122
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DOI: 10.3987/R-1987-12-3115
Definite Total Synthesis of Coumarinolignans, Daphneticin and Its Regioisomer

Hitoshi Tanaka, Masaya Ishijara, Kazuhiko Ichino, and Kazuo Ito

*Faculty of Pharmacy, Meijo University, 150 Yagotoyama, Tenpaku, Nagoya 468-8503, Japan


The synthesis of 7-benzyloxy-8-hydroxycoumarin (5) and 8-benzyloxy-7-hydroxycoumarin (11) was described and further, by use of 5 as a starting material, daphneticin (1) was synthesized. On the other hand, its regioisomer (2) was also synthesized from (8), readily prepared via two steps from 5, according to the method described in the synthesis of daphneticin.

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Paper | Regular issue | Vol 26, No. 12, 1987, pp. 3123 - 3133
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DOI: 10.3987/R-1987-12-3123
A New Route for the Synthesis of 6-Substitutes Imidazo[4-5,c]-1,2,6-thiadiazine 2,2-Dioxides: Nmr Study and Crystal Structure of a Complex with Dimethylformamide

Angela Herrero, Carmen Ochoa, Juan Antonio Páez, Martín Martínez-Ripoll, Concepción Foces-Foces, and Félix Hernadez Cano

*Instituto de Química Médica, C. S. I. C., Calle Juan de Cierva, 3, 28006 Madrid, Spain


The synthesis of.6-substituted imidazo[4,5-c]-1,2,6-thiadiazine 2,2-dioxides from 3,4,5-triamino-1,2,6-thiadiazine 1,1-dioxide and aldehydes is described. 1H- and 13C-nmr studies of the synthesized compounds have been carried out. The crystal structure of the complex formed by the 6-(p-methoxyphenyl) derivative and dimethylformamide has been studied. The imidazothiadiazine ring has an envelope conformation in a packing by hydrogen interactions.

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Paper | Regular issue | Vol 26, No. 12, 1987, pp. 3135 - 3140
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DOI: 10.3987/R-1987-12-3135
Directed Synthesis of 1-Substituted Phenoxazines

Alan R. Katritzky, Luis M. Vazquez de Miguel, and Gordon W. Rewcastle

*Center for Heterocyclic Compounds, Department of Chemistry, University of Florida, P. O. Box 117200, Gainesville, FL 32611-7200, U.S.A.


Phenoxazine protected as its N-lithiocarbamate undergoes lithiation exclusively at the C-1 carbon atom. Reaction of the lithiated species with a variety of alectrophiles readily produces several new 1-substituted phenoxazines, as well as two known compounds in superior yield to those of existing methods.

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Paper | Regular issue | Vol 26, No. 12, 1987, pp. 3141 - 3151
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DOI: 10.3987/R-1987-12-3141
New Methods for the Synthesis of 2-Arylpyrroles

Chris G. Kruse, Jan P. Bouw, Roelof van Hes, Aalt van de Kuilen, and Jack A. J. den Hartog

*Department of Chemistry, Duphar Research Laboratories, PO Box 2, 1380 AA Weesp, The Netherlands


Two short and efficient synthetic approaches for -mostly unknown-2-arylpyrroles are presented. The key intermediates 3 are conveniently obtained from cammercially available acetophenones 5 (method I) or benzoic acid derivatives 10, (method II).

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Paper | Regular issue | Vol 26, No. 12, 1987, pp. 3153 - 3158
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DOI: 10.3987/R-1987-12-3153
An Improved Synthesis of 1-Alkyl-4-imidazolin-2-ones

Ooi Wong, Noriko Tsuzuki, Mark Richardson, Howard Rytting, Ryoji Konishi, and Takeru Higuchi

*Department of Pharmaceutical Chemistry, University of Kansas, 4070 Malott Hall, Lawrence, Kansas 66045-2506, U.S.A.


Two 1-alkyl-4-imidazolin-2-ones were prepared by acid-catalysed cyclization of N-(2,2-dialkoxyethyl)-N-alkylureas, with improved yields of over 90%. The amount of HC1 used in the reaction and the proper isolation procedure are the important factors in obtaining the high yields.

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Paper | Regular issue | Vol 26, No. 12, 1987, pp. 3159 - 3164
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DOI: 10.3987/R-1987-12-3159
Nucleophilic Substitution Reactions on Sulfur by n-Butyllithium 2

Toshiyasu Mase and Kiyoshi Murase

*Central Research Laboraories, Yamanouchi Pharmaceutical Co., Ltd., 1-1-8, Azusawa, Itabashi-ku, Toyko 174-0051, Japan


The reaction of some 2-phenylimidazo[2,1-b]benzothiazoles (1) with organometal reagents (n-BuLi, n-Bu2CuLi, i-Pr2NLi and EtMgBr) has been investigated. Two reagents (n-BuLi and n-Bu2CuLi) induced the nucleophilic substitution reaction on sulfur of 1 and to give the C-S bond cleaved compounds.

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Paper | Regular issue | Vol 26, No. 12, 1987, pp. 3165 - 3172
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DOI: 10.3987/R-1987-12-3165
Synthesis of 1,2,3,4,4a,5,9,10,16,16a-Decahydro-2-methyl[1]benzazepino [3,2,1-jk]Pyrido[3,4-b][1]benzazepine: A Conformationally Rigid Imipramine Analog

Philip G. Dunber and Arnold R. Martin

*Department of Pharmaceutical Sciences, College of Pharmacy, The University of Arizona, Tucson, AZ 85721, U.S.A.


Ortho lithiations and acylations of 10,11-dihydro-5H-dibenz[b,f]azepine and N,N-diethylnicotinamide respectively led to the convenient synthesis of the key intermediate 4-[(10,11-dihydro-5H-dibenz[b,f]azepin-4-yl)hydroxymethyl]-N,N-diethylnicotinamide 2a, Catalytic reduction of 2, and subsequent cyclization of the resulting carboxylic acid 3, provided the pentacyclic lactam 4 required for further elaboration of the rigid imipramine analog. Difficulties in amide hydrolysis are discussed. Further reductions and N-methylation provided both cis and trans ring fusion isomers 8a and 8b identified by 1H and 13C nmr.

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Paper | Regular issue | Vol 26, No. 12, 1987, pp. 3173 - 3180
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DOI: 10.3987/R-1987-12-3173
Cycliaddition Reactions of 2,3-Diphenylquinoxaline-5,8-dione. Synthesis of Novel Pyrazolo[3,4-g]quinoxalinequinone, Isoxazolo[4,5-g]quinoxalinequinone and Pyrrolo[3,4-g]quinoxalinequinone

Bindumadhavan Venugopalan, Sivasilam Suresh Iyer, Pravin Jayant Karnik, and Noel John de Souza

*Department of Chemistry, Research Centre, Hoechst India Limited, Mulund, Bombay 400 080, India


2,3-Disubstituted quinoxalinequinones were prepared. Synthesis of pyrazolo [3,4-g]quinoxalinequinones 4 and 5, isoxazolo [4,5-g]quinoxalinequinone 7 and pyrrolo [3,4-g]quinoxa1inequinone 10 using dipolar cycloaddition reactions of quinoxalinequinones 3 with respective dipoles are reported.

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Paper | Regular issue | Vol 26, No. 12, 1987, pp. 3181 - 3191
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DOI: 10.3987/R-1987-12-3181
Synthesis of Arglecin

Akihiro Ohta, Yutaka Aoyagi, Yohko Kurihara, Kayo Yuasa, Makoto Shomazaki, Teruo Kurihara, and Hiroshi Miyamae

*Tokyo University of Pharmacy and Life Science, 1432-1 Horinouchi, Hachioji, Tokyo 192-0392, Japan


Arglecin (1) and its analogue, 6-(3-aminopropy1)-3-isobutyl-2(1H)-pyrazinone (2). were synthesized from DL-alanyl-leucyl anhydride in several steps.

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Paper | Regular issue | Vol 26, No. 12, 1987, pp. 3193 - 3196
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DOI: 10.3987/R-1987-12-3193
A Facile Preparation of 3-Substituted 2-Thioxo-tetrahydoquinazolin-4-ones by the Reaction of Anthranilamide with Isothiocynates

Chao-Han Chan, Fang-Jy Shish, Kang-Chien Liu, and Ji-Wang Chern

*Medical Laboratories and Institute of Pharmacy, National Defense Medical Center, P.O. Box 90048-512, Taipei, Taiwan, R.O.C.


3-Substituted 2-thioxa-tetrahydroquinazolin-4-ones (4a-d) can be synthesized in a convenient procedure directly by a treatment of anthranilemide with isothiocyanates at room temperature. However, anthranilamide was reacted with 4-isothiocyanato-1-benzylpiperidme (2e) leading to the formation of 2-[3-(1-benzyl-4-piperidinyl)]thioureidobenzarnide (3e) which was subsequently cyclized to 4e under a basic condition.

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Paper | Regular issue | Vol 26, No. 12, 1987, pp. 3197 - 3202
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DOI: 10.3987/R-1987-12-3197
The [3+2] Cycloaddition Reaction of Nonstabilized Azomethine Ylide Generated from Trimetylmine N-Oxide to C=C, C=N, and C=S Bonds

René Beugelmans, Jacqueline Chastanet, and Georges Roussi

*Institut des Chimie des Substances Naturelles, C.N.R.S., 1 avenue de la Terrasse, Bat. 27, 91198 Gif-sur-Yvette Cedex, France


The reported cycloaddition reactions between nonstabilized azomethine ylide Y generated from trimethylamine N-oxide 1 and unactivated C≡C 2 - 4, C=N 5 and C=S 6, 7 bonds constitute an attractive entry respectively to pyrrolines and pyrroles 10 - 13, imidazalidine 14 and thiazolidines 15, 16.

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Paper | Regular issue | Vol 26, No. 12, 1987, pp. 3203 - 3209
Published online:
DOI: 10.3987/R-1987-12-3203
Stereochemistry of Diastereomeric 9,10-Dimethoxy-1,3,4,6,7,11b-hexahydrospiro[banzo[a]quinolizin-2,5‘-imidazolidine]-2‘,4‘-diones

J. Carlos Meréndez and Mónica M. Söllhuber

*Departamento de Química Orgánica y Farmacéutica, Facultad de Farmacia, Universidad Complutense de Madrid, Ciudad Universitaria, 28040 Madrid, Spain


The structures of the two diastereomeric title compounds obtained by the Bucherer-Bergs and Read procedures are respectively assigned to α and β isomers on the basis of 1H -nmr, 13C-nmr and chemical reactivity data. Both compounds present a predominant trans conformation as shown by ir, 1H-nmr and 13C-nmr data.

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Paper | Regular issue | Vol 26, No. 12, 1987, pp. 3211 - 3220
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DOI: 10.3987/R-1987-12-3211
Polycyclic N-Hetero Compounds. XXX. Synthesis and Antidepressive Evaluation of 3-Substituted 3,4,5,6-Tetrahydrobenzo[h]quinazolin-4-ones

Takashi Hirota, Kenji Sasaki, Hiroshi Yamamoto, and Takashi Katsu

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


Syntheeis of 3-substituted 3,4,5,6-tetrehydrohenzo[h]-quinaeolin-4-ones is described. Antidepressive evaluation of these compounds was performed by antireserpine action and compounds IX and X exhibited the positive action.

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Paper | Regular issue | Vol 26, No. 12, 1987, pp. 3221 - 3227
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DOI: 10.3987/R-1987-12-3221
Photochemical Route to Cyclobut[b]isoxazolo[4,5-e]pyridine, a New Heterocyclic System

Giorgio Adembri, Donato Donati, Stefania Fusi, and Fabio Potticelli

*Istituto di Chimica Organica, Università di Siena, Pian dei Mantellini 44, 53100 Siena, Italy


Photochemical adducts between 3-carbamoyl- or 3-ethoxycarbonyl- 1-benzyl-1,4-dihydropyridine and CH2=CH-CN were transformed to derivatives of title compound (6a,b and 7a,b) via regio- and stereospecific 1,3-dipolar addition of p-C1-benzonitriloxide. Isomers 8 and 9 with inverted configuration at carbon bearing CN group can be obtained in EtOH/EtO- solution.

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Paper | Regular issue | Vol 26, No. 12, 1987, pp. 3229 - 3231
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DOI: 10.3987/R-1987-12-3229
A Convenient Synthesis of 3-Aryl Coumarins

Yang Ming and David W. Boykin

*Department of Chemistry, Georgia State University, University Plaza, Atlanta, GA 30303, U.S.A.


A new, convenient, one-step synthesis of 3-aryl coumarins from 2-fluorobenzaldehyde and aryl acetic acids is reported.

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Paper | Regular issue | Vol 26, No. 12, 1987, pp. 3233 - 3237
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DOI: 10.3987/R-1987-12-3233
A Convenient Route to 6-Aminocyclopenta[b]thiophene Derivatives

Patrick Dallemagne, Sylvain Rault, Marina Gordaliza, and Max Robba

*Departamento de Química Orgánica y Farmacéutica, Facultad de Farmacia, Universidad de Salamanca, Av. Campo Charro s.n. 37007-Salamanca, Spain


The intramolecular cyclization of 3-amino-3-(2-thienyl) propionic acid to 6-amino-5,6-dihydrocyclooenta[b] thiophene was achieved by Friedel-Crafts reaction.

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34 data found. 1 - 30 listed Next Last