Regular Issue

Vol. 36, No. 5, 1993

26 data found. 1 - 26 listed
Communication | Regular issue | Vol 36, No. 5, 1993, pp. 923 - 927
Published online:
DOI: 10.3987/COM-92-6230
Study of Thiazolo[4,5-d]pyrimidines: The Synthesis of Thiazolo[4,5-d]pyrimidine-2,7-diones and Novel Ring Opening to 2,4-Thiazolidinedione

Katsuhiko Nagahara,* Masae Sekine, Atsushi Takada, Howard B. Cottam, and Roland K. Robins

*School of Pharmaceutical Sciences, Kitasato University, Shirokane, Minato-ku, Tokyo 108-8641, Japan


Treatment of 7-oxo-3-phenylthiazolo[4,5-d]pyrimidine-2(6H)-thione (1) with dimethyl sulfate afforded 6-methyl-3-phenylthiazolo[4,5-d]pyrimidine-2,7-dione (2), 3-phenylthiazolo[4,5-d]pyrimidine-2,7(6H)-dione (3) and/or 5-N-methylcarbamoyl-3-phenyl-2,4-thiazolidinedione (5), depending on reaction conditions. Furthermore, reaction of 3 with dimethyl sulfate caused the ring opening to give corresponding 5. Also, treatment of 5 with phosphorus oxychloride gave 4-chloro-2-oxo-3-phenylthiazolidine-5-N-methylcarboxamide (6).

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Communication | Regular issue | Vol 36, No. 5, 1993, pp. 929 - 932
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DOI: 10.3987/COM-92-6294
Highly Diastereomer Selective Acylation of 2,5-Dialkylpyrrolidines. A Versatile Route to trans-2,5-Disubstituted Cyclic Amino Alcohols

Anne Fleurant, Cyrille Grandjean, Olivier Provot, Sylvie Rosset, Jean Pierre Célérier, and Gérard Lhommet*

*Université Pierre et Marie Curie, Laboratoire de Chimie des Hétérocycles, Aassocie au CNRS, URA 408, 4, Place Jussieu, F-75252 Paris Cedex 05, France


Diastereoisomeric mixtures of cis- and trans- disubstituted pyrrolidines are separated by kinetically controlled acylation with benzyl chloroformate.

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Communication | Regular issue | Vol 36, No. 5, 1993, pp. 933 - 936
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DOI: 10.3987/COM-92-6297
Structure of Novel Antioxidative Lignan Triglucoside Isolated from Sesame Seed

Hirotaka Katsuzaki, Shunro Kawakishi, and Toshihiko Osawa*

*Department of Food Science and Technology, Nagoya University, Chikusa, Nagoya, Aichi 464-8601, Japan


A new lignan triglucoside was isolated from sesame seed. This compound had branched (1→ 2)- and (1→ 6)-glucosidic linkage, and showed antioxidative activity.

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Communication | Regular issue | Vol 36, No. 5, 1993, pp. 937 - 940
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DOI: 10.3987/COM-92-6307
Highly Enantioselective Reduction of meso-Cyclic-1,2-dicarboximides. Asymmetric Synthesis of Bicyclic 2-Pyrrolidinone and Its 5-Hydroxy Congener

Kenji Matsuki,* Hirozumi Inoue, Akihiko Ishida, Mikio Takeda, Masako Nakagawa, and Tohru Hino

*Organic Chemistry Research Laboratory, Tanabe Seiyaku Co.Ltd., 2-2-50, Kawagishi, Toddda, Saitama 335-8505, Japan


Bicyclic 5-hydroxy-2-pyrrolidinones (2a-f) were synthesized with high enantioselectivity by the reduction of meso-cyclic-1,2-dicarboxiamides (1a-f) with lithium aluminum hydride (LiAlH4)-methanol (MeOH)-1,1’-bi-2-naphthol complex (BINAL-H). Treatment of 2a-f with triethylsilane (Et3SiH) and trifluoroacetic acid (CF3CO2H) gave optically active 2-pyrrolidinones (3a-f) in quantitative yields. For the absolute configuration correlation, 2a-d were converted into known lactones (4a-d).

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Communication | Regular issue | Vol 36, No. 5, 1993, pp. 941 - 942
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DOI: 10.3987/COM-92-6314
Preparation and Arylation of 2-Indolylzinc Derivatives

Takao Sakamoto,* Yoshinori Kondo, Nobuo Takazawa, and Hiroshi Yamanaka*

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


2-Arylindoles were synthesized by the palladium-catalyzed reaction of aryl halides with 2-indolylzinc derivatives which were derived from the lithio derivatives.

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Communication | Regular issue | Vol 36, No. 5, 1993, pp. 943 - 946
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DOI: 10.3987/COM-92-6321
Total Synthesis of Kuanoniamine A, 11-Hydroxyascididemin, and Neocalliactine Acetate

Yoshiyasu Kitahara, Shinsuke Nakahara, Takanobu Yonezawa, Masanori Nagatsu, and Akinori Kubo*

*Meiji College of Pharmacy, 1-35-23 Nozawa, Setagaya-ku, Tokyo 154, Japan


A pentacyclic aromatic alkaloid, kuanoniamine A (5) was synthesized from 6-methoxybenzothiazole-4,7-dione (7) and 2-aminoacetophenone (8). Similarly, 11-hydroxyascididemin (4) was prepared from 6-bromo-4-chloro-5,8-dimethoxyquinoline (12). The structure of neocalliactine acetate, a derivative of calliactine, was determined as 19 by total synthesis from 6-methoxy-5,8-quinolinedione (23) and 2-amino-5-methoxyacetophenone (24).

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Paper | Regular issue | Vol 36, No. 5, 1993, pp. 947 - 959
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DOI: 10.3987/COM-92-6079
Synthesis and Reactions of Some 3-Cyano-4-methylcoumarins

Hassan M. F. Madkour

*Department of Chemistry, Faculty of Science, Ain Shams University, Abbassiya 11566, Cairo, Egypt


O-Hydroxy ketones (I) were converted into 3-cyano-4-methylcoumarins (II) via condensation with ethyl cyanoacetate in presence of piperidine or ammonium acetate as a catalyst. The behavior of compound (II) towards Grignard and Michael reactions was investigated. The reactions of 3-acetylcoumarin (III) with hydrazines under different conditions were carried out to give the hydrazone (VI a), phenylhydrazone (IV b) and pyrazole (V) derivatives. Also, the 4-styryl derivatives (VI) were obtained by condensation of II with different aromatic and heterocyclic aldehydes. A one pot synthesis of Michael product (VII) from the reaction of VI with malononitrile was described.

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Paper | Regular issue | Vol 36, No. 5, 1993, pp. 961 - 969
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DOI: 10.3987/COM-92-6152
Synthesis of Organofluorine Compounds Utilizing 3-[1-(3-Fluorophenylhydrazono)-D-erythro-2,3,4-trihydroxybutyl]quinoxalin-2(1H)-one as a Precursor

Nagwa Rashed,* Hamida Abdel Hamid, and Mahmoud Shoukry

*Department of Chemistry, Faculty of Science, Alexandria University, P.O. Box 426, Ibrahimia, Alexandria 21321, Egypt


The reaction of D-erythro-2,3-hexodiulosono-1,4-lactone with 1,2-diaminobenzene followed by 3-fluorophenylhydrazine and the reaction of the product with dimethyl sulfate, sodium metaperiodate and acetic anhydride in pyridine have been investigated. The isopropylidenation of 3-[1-(3-fluorophenylhydrazono)-D-erythro-2,3,4-trihydroxybutyl]quinoxalin-2(1H)-one under thermodynamic controlled conditions has been studied. Compounds 3-[1-(3-fluorophenylhydrazono)-D-erythro-2,3,4-trihydroxybutyl]quinoxalin-2(1H)-one and its N-methyl derivative undergo dehydrative cyclisation in boiling acetic anhydride to the corresponding pyrazolylquinoxalinones.

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Paper | Regular issue | Vol 36, No. 5, 1993, pp. 971 - 985
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DOI: 10.3987/COM-92-6224
Site Selective Alkoxymethylation of Imidazo[4,5-b]pyridines: Structural Analysis by High Field NMR Methods

Malvinder P. Singh, Yadagiri Bathini, and J. William Lown*

*Department of Chemistry, University of Alberta, Edmonton, Alberta, T6G 2G2, Canada


The alkylation reactions of 2-aryl-1(3)H-imidazo[4,5-b]pyridines (eauivalent to 1-deazapurines) with alkoxymethyl chlorides and bromoacetonitrile are described. The structural assignments of the products were made by the use of two-dimensional 1H-1H NOE (NOESY) and selective INEPT (INAPT) 13C nmr experiments utilizing polarization transfer from carbon-bound hydrogens in the alkyl side chains to selected 13C resonances via long-range 3JCH couplings. Although three isomeric N-alkyl derivatives could arise from a single heterocycle based on considerations of tautomeric equillibria, however, the reactions exhibit marked site selectivity even under quite different reaction conditions. Thus, N-3 alkyl derivatives are produced exclusively in basic (Et3N/NaH) nonpolar media following and an SE2cB mechanism. Solvent effects are evident in a loss of N-3 vs N-1 selectivity for alkylation when the polar aprotic solvent DMF is used. Under neutral conditions direct alkylation occurs at the N-4 position following an SE2’ mechanism. The overall site selectivity appears to be governed by the relative reactivity of individual nucleophilic sites rather than the tautomeric composition in solution.

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Paper | Regular issue | Vol 36, No. 5, 1993, pp. 987 - 993
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DOI: 10.3987/COM-92-6247
A Novel Synthetic Route to Cyanophenothiazines. First Example of Smiles Rearrangement from Halogenobenzonitriles

Yvette Mettey and Jean-Michel Vierfond*

*Laboratoire de Chimie Organique,GREAM, Faculte de Pharmacie,BP 199, 34 rue du Jardin des Plantes, 86005 Poitiers Cedex, France


The reaction of halogenobenzonitriles with 2-aminobenzenethiol gave, by a Smiles rearrangement 2-mercaptocyanodiphenylamines which are cyclised to cyanophenothiazines via a disulfide intermediate. A mechanism is proposed.

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Paper | Regular issue | Vol 36, No. 5, 1993, pp. 995 - 1003
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DOI: 10.3987/COM-92-6256
Structures of Saturated Azeto[1,2-a][3,1]- and Azeto[2,1-b][1,3]benzoxazines Prepared by Addition of Chloroacetyl Chlorides to Cyclohexane-condensed Dihydrooxazines

Géza Stájer, Angela E. Szabó, Ferenc Fülöp, Gábor Bernáth,* and Pál Sohár

*Institute of Pharmaceutical Chemistry, Albert Szent-Györgyi Medical University, H-6701 Szeged, Eötvö;s u.6., Hungary


Saturated cis and trans 3,1- and 1,3-benzoxazines (1-4) reacted with chloroacetyl chlorides to yield azeto[1,2-a][3,1]- and [2,1-b][1,3]benzoxazines (5, 6, 8, 9a,b). In one case, the addition took place with partial cistrans inversion of the starting compound. Adduct (7), containing two condensed 1,3-oxazine rings, was also isolated. The stereostructures of the new compounds were proved by 1H- and 13C-nmr spectroscopy, with NOE measurement data. The reaction mechanism is discussed.

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Paper | Regular issue | Vol 36, No. 5, 1993, pp. 1005 - 1016
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DOI: 10.3987/COM-92-9259
Synthesis of 2,3-Fused Quinolines from 3-Substituted Quinoline 1-Oxides. Part II.

Yutaka Miura,* Mitsutaka Yoshida, and Masatomo Hamana

*Exploratory Laboratories, Chugai Pharmaceutical Company, Ltd., 1-135 Komakado, Gotemba, Shizuoka 412-835, Japan


3-Bromo-4-nitroquinoline 1-oxide (1) reacted with 2-methylaminoethanol, 1-amino-2-propanol and ethylenediamine to give the corresponding 3-amino-4-nitroquinoline 1-oxides (2, 4 and 7), which readily underwent the intramolecular cyclization, upon heating with Ac2O in DMF, to afford the morpholino[2,3-b]quinolines (3 and 6) and the piperazino[2,3-b]quinoline (8). The reaction of 1 with N,N’-dimethylethylenediamine afforded directly the piperazinoquinoline (10), and that with 2-aminoethanethiol gave the thiomorpholino[2,3-b]quinoline (11) and its 10-oxide (12).

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Paper | Regular issue | Vol 36, No. 5, 1993, pp. 1017 - 1026
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DOI: 10.3987/COM-92-9262
Synthesis of (+)-trans-Whisky Lactone, (-)-cis-Whisky Lactone, (+)-Cognac Lactone and (+)-Eldanolide

Takashi Ebata,* Katsuya Matsumoto, Hajime Yoshikoshi, Koshi Koseki, Hiroshi Kawakami, Koji Okano, and Hajime Matsushita

*Life Science Research Laboratory, Japan Tobacco Inc., 6-2, Umegaoka, Midori-ku, Yokohama, Kanagawa 227-8512, Japan


(+)-trans-Whisky lactone (5) and (-)-cis-whisky lactone (8), (+)-cognac lactone (9) and (+)-eldanolide (10) were synthesized starting from levoglucosenone (1) in optically pure states.

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Paper | Regular issue | Vol 36, No. 5, 1993, pp. 1027 - 1038
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DOI: 10.3987/COM-92-6263
Synthesis of N-Alkyl-1,2,4-oxadiazinones as Angiotensin-II (AT1) Receptor Antagonists

Harold N. Weller,* Arthur V. Miller, Kenneth E. J. Dickinson, S. Anders Hedberg, Carol L. Delaney, Randolph P. Serafino, and Suzanne Moreland

*Bristol-Myers Squibb Pharmaceutical Research Institute, P.O. Box 4000, Princeton, NJ 08543-4000, U.S.A.


4-Alkyl-1,2,4-oxadiazinones were prepared by regiospecific alkylation of the corresponding 4H-oxadiazinones, which were synthesized by a trimethylaluminum mediated cyclization reaction. Alkylation was regiospecific and generally facile; in one example, however, an unusual fragmentation reaction occurred. A homochiral oxadiazineone was also prepared and alkylated under the described conditions. 4-Biphenylmethyl-1,2,4-oxadiazinones were potent angiotensin-II receptor antagonists.

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Paper | Regular issue | Vol 36, No. 5, 1993, pp. 1039 - 1046
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DOI: 10.3987/COM-92-6265
Norrish Type II Photo-Deacylation of Semicyclic Imides

Akira Sera,* Manabu Okada, Akira Ohhata, Hiroaki Yamada, Kuniaki Itoh, and Yasuo Kubo

*Department of Chemistry, Faculty of Science, Kobe University, Nada-Ku, Kobe 6557-8501, Japan


The photochemical deacylation of 1,4-diacyl-2,5-piperazinediones was found to proceed through the type II ketene eliminating process.

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Paper | Regular issue | Vol 36, No. 5, 1993, pp. 1047 - 1050
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DOI: 10.3987/COM-92-6268
Improved Synthesis of Dihydroisoquinoline Reissert Compounds

Yvette A. Jackson, E. Kyle Stephenson, and Michael P. Cava*

*Department of Chemistry, The University of Alabama, Box 870336, Tuscaloosa Alabama 35487-0336, U.S.A.


Conversion of a series of 3,4-dihydroisoquinolines to their corresponding Reissert compounds was improved significantly over the usual reaction conditions by buffering the reaction medium at pH 8.

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Paper | Regular issue | Vol 36, No. 5, 1993, pp. 1051 - 1058
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DOI: 10.3987/COM-92-6271
Synthesis of Indanyl Analogs of 3-[3-(4-Arylpiperazin-1-yl)propyl]-2-oxo-2,3-dihydro[1,3]benzoxazoles

Patrick Depreux, Hocine Aichaoui, and Isabelle Lesieur*

*Laboratorie de Chimie Théraqeutique, Faculté Pharmcie, Université de Lille 2, 3, rue du Professeur Laguesse, BP 83, 59006 Lille Cedex, France


Original indanyl analogs of 3-[3-(4-arylpiperazin-1-yl)propyl]-dihydro-2-oxo[1,3]benzoxazoles were synthesized from 6-acyl-2-oxo-2,3-dihydro[1,3]benzoxazoles.

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Paper | Regular issue | Vol 36, No. 5, 1993, pp. 1059 - 1064
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DOI: 10.3987/COM-92-6274
Reaction of 1-Methylpyrrole with 1,3-Dichloro-5,5-disubstituted Hydantoins: Products and AM1 Study of Intermediates

Michael De Rosa,* Edward Melenski, and Andrew J. Holder

*Department of Chemistry, The Pennsylvania State University Delaware County Campus, 25 Yearsley Mill Road, Media, PA 19063, U.S.A.


The reaction of 1-methylpyrrole with 1,3-dichloro-5,5-dimethylhydantoin gave 3-(1-methyl-1H-pyrrol-2-yl)-5,5-dimethylhydantoin and 1,3-di-(1-methyl-1H-pyrrol-2-yl)-5,5-dimethylhydantoin as products. In contrast reaction with 1,3-dichloro-5-methyl-5-phenylhydantoin (3) or 1,3-dichloro-5,5-diphenylhydantoin (4) gave only the monopyrroylhydantoin derivatives. This difference was attributed to a steric interaction between the substituents on C-5 and N1.

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Paper | Regular issue | Vol 36, No. 5, 1993, pp. 1065 - 1074
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DOI: 10.3987/COM-92-6276
Synthesis of 6,7-Dihydro-8-(4-methyl-1-piperazinyl)-[1]benzoxepino[4,5-c]quinoline as Potential 5-HT3 Receptor Ligand

Maurizio Anzini,* Andrea Cappelli, and Salvatore Vomero

*Dipartimento Farmaco Chimico Technlogico, Università degli Studi di Siena, Banchi di Sotto, 55 - 53100 Siena, Italy


Two synthetic routes to the achievement of the title compound are described. The [1]benzoxepino[4,5-c]quinoline nucleus was prepared by nucleophilic aromatic fluoride displacement-cyclization and functionalized with N-methylpiperazine moiety. Alternatively the oxepino ring closure is shifted as the final step. An oxepine ring cleavage occurred in compounds (9) and (3); a mechanistical interpretation is proposed.

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Paper | Regular issue | Vol 36, No. 5, 1993, pp. 1075 - 1080
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DOI: 10.3987/COM-99-6278
A Very Simple Oxidation of Olefins and Ketones with UHP-Maleic Anhydride

Luis Astudillo, Antonio Galindo,* Antonio G. González, and Horacio Mansilla

*Centro de Productos Naturales Orgánicos "Antonio González", Universidad de La Laguna, Avda. Astrofísico Franciso Sánchez, 2, 38206- La Laguna, Tenerife, Spain


The oxidation of olefins and ketones to oxiranes and esters, respectively, is carried out with the UHP (urea-hydrogen peroxide complex) - maleic anhydride system in a mild and very simple procedure.

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Paper | Regular issue | Vol 36, No. 5, 1993, pp. 1081 - 1089
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DOI: 10.3987/COM-92-6277
New Alkaloids from Consolida hellespontica

Haridutt K. Desai, Balawant S. Joshi, S. William Pelletier,* Bilge Sener, Funda Bingöl, and Turan Baykal

*Institute for Natural Products Research, Department of Chemistry, The University of Georgia, Chemistry Building, Athens, Georgia 30602-2556, U.S.A.


From the aerial parts of Consolida hellespontica (Boiss.) Chater we have isolated the new diterpenoid alkaloids chellespontine (1) and azitine (4). The norditerpenoid alkaloid 1-O-methyldelphisine (7) has not been reported earlier as occurring in nature, and the aporphine alkaloid (+)-corydine (11) has been isolated for the first time in the Ranunculaceae family. Besides these, the known alkaloids delphinine (8), delphisine (9) and bullatine C (14-acetylneoline) (10) have been isolated from this plant. The structures of these alkaloids were established by chemcial correlation and spectroscopic studies.

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Paper | Regular issue | Vol 36, No. 5, 1993, pp. 1091 - 1103
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DOI: 10.3987/COM-92-6285
Studies on 1,2,4-Benzothiadiazine 1,1-Dioxides VII and Quinazolinones IV: Synthesis of Novel Built-In Hydroxyguanidine Tricycles as Potential Anticancer Agents

Ji-Wang Chern,* Yen-Chywan Liaw, Chien-Shu Chen, Jiann-Gwo Rong, Chien-Lin Huang, Chao-Han Chan, and Andrew H.-J. Wang

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


Two representative built-in hydroxyguanidine tricycles containing 1,2,4-benzothiadiazine 1,1-dioxides (3) and quinazolinones (4) were prepared by reductive cycliazation of 1-(2-nitrophenylsulfonyl)-2-benzylthio-2-imidazoline (9a), 1-(2-nitrophenylsulfonyl)-2-benzylthio-1,4,5,6-tetrahydropyrimidine (9b), 1-(2-nitrobenzoyl)-2-benzylthio-2-imidazolidine (10a) and 1-(2-nitrobenzoyl)-2-benzylthio-1,4,5,6-tetrahydropyrimidine hydrobromide respectively (10b) with zinc dust in acetic acid under ice-cooling. 2,10-Dihydro-10-hydroxy-3H-imidazo[1,2-b][1,2,4]benzothiadiazine 5,5-dioxide (3a) and 2,3,4,11-tetrahydro-11-hydroxypyrimido[1,2-b][1,2,4]benzothiadiazine 6,6-dioxide (3b) were found to be active against solid tumor cell lines such as KB, Colo 205, HeLa, and Hepa-2.

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Paper | Regular issue | Vol 36, No. 5, 1993, pp. 1105 - 1113
Published online:
DOI: 10.3987/COM-92-6287
Preparation of [1]Pyrido[3’,2’:5,6]thiopyrano[4,3,2-de]quinoline

Hidetoshi Fujiwara* and Ichizo Okabayashi

*Niigata College of Pharmacy, 5-13-2 Kamishin’ei-cho, Niigata 950-2081, Japan


New tetracyclic compound, pyrido[3’,2’:5,6]thiopyrano[4.3,2-de]quinoline (1) was synthesized from 6-amino-5H-[1]benzothiopyrano[2,3-b]pyridin-5-one (2) in a ten step sequence.

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Paper | Regular issue | Vol 36, No. 5, 1993, pp. 1115 - 1126
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DOI: 10.3987/COM-92-6299
Short, Stereoselective Synthesis of Na-Boc-5β-cyanodeformyl-Z-geissoschizine, a Prototype of Potential Synthons in the Preparation of Sarpagan and Ajmalan Ring System

Reija Jokela, Minna Halonen, and Mauri Lounasmaa*

*Laboratory for Organic and Bioorganic Chemistry, Technical University of Helsinki, P.O. Box 6100, SF-02150 Espoo, Finland


This paper describes a short, easy synthesis of Na-Boc-5β-cyanodeformyl-Z-geissoschizine (4), a prototype of potential synthons in the preparation sarpagan and ajmalan ring systems.

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Paper | Regular issue | Vol 36, No. 5, 1993, pp. 1127 - 1138
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DOI: 10.3987/COM-92-6312
Nucleophilic Radical Substitution of Polychloroazines

Nobuhiro Kanomata, Mamoru Igarashi, and Masaru Tada*

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


Polychloroazines (1-6) are susceptible to homolytic chlorine substitution by alkyl radicals. In general, the chlorine at the ortho-position to the ring nitrogen is readily replaced by an alkyl radical like adamantyl and tert-butyl. However, the chlorine at the C2-position of pyrimidine did not show any sign of the radical substitution. The reactivity decreases in the order of adamantyl, tert-butyl, and isopropyl radicals.

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Paper | Regular issue | Vol 36, No. 5, 1993, pp. 1139 - 1144
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DOI: 10.3987/COM-92-6322
Total Synthesis of Eilatin

Shinsuke Nakahara, Yoshihiro Tanaka, and Akinori Kubo*

*Meiji College of Pharmacy, 1-35-23 Nozawa, Setagaya-ku, Tokyo 154, Japan


Synthesis of the symmetrical pentacyclic fused aromatic alkaloid called eilatin (1) is described.

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26 data found. 1 - 26 listed