Special Issue

Yoshio Ban's Special Issues, Vol. 42, No. 2, 1996

46 data found. 1 - 30 listed Next Last
Communication | Special issue | Vol 42, No. 2, 1996, pp. 475 - 478
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DOI: 10.3987/COM-95-S58
Asymmetric Dialkylation of Chiral 2-Benzazepine Formamidines

A. I. Meyers and Richard Hutchings

*Department of Chemistry, Colorado State University, Fort Collins, CO 80523-1872, U.S.A.


Repeated metallation and alkylation of an (S)-(+)-tertleucinol derived 2,3,4,5-tetrahydro-1H-2-benzazepine formamidine leads to the corresponding 1,1 -dialkyl-2-benzaepines in good yields and with excellent enantioselectivities.

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Communication | Special issue | Vol 42, No. 2, 1996, pp. 479 - 484
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DOI: 10.3987/COM-95-S65
Biotransformation of Dibenzylbutanolides by Peroxidase Enzymes. Routes to the Podophyllotoxin Family.

James P. Kutney, Xinyao Du, Rajina Naidu, Nikolay M. Stoynov, and Masumi Takemoto

*Department of Chemistry, The University of British Columbia, 2036 Main Mall, Vancouver B.C., V6T 1Z1, Canada


In continuing studies on enzyme-catalyzed cyclization of synthetic dibenzylbutanolides to members of the podophyllotoxin family, experiments which involve the biotransformation of such synthetic substrates with horseradish peroxidase and with enzymes produced by the cell culture of Nicotiana sylvestris are presented. Cyclization of synthetic 3 to the desired 5 proceeds efficiently with purified horseradish peroxidase enzyme but not with the acetone powder. A much preferred route to 5, in gram scale synthesis, involves the biotransfonnation of 3 with the enzymes produced by the cell culture of Nicotiana sylvestris. This stable cell line, when grown in bioreactors, produces sufficient quantities of enzyme for efficient multi-gram synthesis in short time incubations (5-30 min). The application of this methodology for production of podophyllotoxins utilized as starting materials in etoposide synthesis is under study in our laboratory.

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Communication | Special issue | Vol 42, No. 2, 1996, pp. 485 - 488
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DOI: 10.3987/COM-95-S71
A Mild and Rapid Glycosylation Reaction between Pyrimidine Bases and 2-Deoxyribofuranosyl N,N,N',N'-Tetramethylphosphoroamidates

Takamasa Iimori, Hiroshi Kobayashi, Shun-ichi Hashimoto, and Shiro Ikegami*

*Faculty of Pharmaceutical Sciences, Teikyo University, 1091-1 Suarashi, Sagamiko-machi, Tsukui-gun, Kanagawa 199-0195, Japan


A trimethylsilyl triflate-mediated coupling reaction to produce protected 2’-deoxynucleosides has been developed by using N,N,N’,N’-tetramethylphosphoroamidate as a leaving group. In this reaction, employment of a 3,4,5-trimethoxybenzoyl group as the 3-hydroxyl protective group in the sugar moiety improved the β-stereoselectivity via a novel 1,3-participation.

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Communication | Special issue | Vol 42, No. 2, 1996, pp. 489 - 492
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DOI: 10.3987/COM-95-S72
The Mechanism of Configuration Retention in the Substitution Reaction of C4-Tosyloxyproline with Lithium Diarylcuprate

Kimiko Hashimoto, Yukio Shima, and Haruhisa Shirahama*

*Department of Chemistry, Faculty of Science, Hokkaido University, Sapporo 060-0810, Japan


The mechanism of configuration retention during the substitution reaction of C4-tosyloxyproline with lithium diarylcuprate was studied. Among the three possible intermediates (a~c), c has been found to be the origin of the retention mechanism.

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Communication | Special issue | Vol 42, No. 2, 1996, pp. 493 - 497
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DOI: 10.3987/COM-95-S74
Total Synthesis of (-)-Qinghaosu IV (Artemisinin D, Arteannuin D)

Hsing-Jang Liu* and Wen-Lung Yeh

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


Starting from (-)-β-pinene (3), a total synthesis of (-)-qinghaosu IV (1) has been accomplished.

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Communication | Special issue | Vol 42, No. 2, 1996, pp. 499 - 502
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DOI: 10.3987/COM-95-S78
Practical Radical Deoxygenation of Erythromycins by Barton Reaction

Tsutomu Sato, Hiroshi Koga, and Koichi Tsuzukli

*Fuji Gotemba Research Laboratories, Chugai Pharmaceutical Company, Ltd., 135, 1-Chome Komakado, Gotemba City, shizuoka 412-8513, Japan


Practical radical deoxygenation method of erythromycins was established. Macrolide-type motilin receptor agonist GM-665 (1) has been prepared using this method.

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Communication | Special issue | Vol 42, No. 2, 1996, pp. 503 - 508
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DOI: 10.3987/COM-95-S79
One-Step Synthesis of (-)-5-epi-Hydantocidin

Noriyuki Nakajima, Masayuki Kirihara, Miyoko Matsumoto, Masaru Hashimoto, Tadashi Katoh, and Shiro Terashima

*Sagami Central Research Center, Nishi-Ohnuma, Sagamihara, Kanagawa 229-0012, Japan


One-step synthesis of (-)-5-epi-hydanrocidin was achieved by heating a mixture of D-isoascorbic acid and urea without solvent. Studies on N,O-spiroketal formation and epimerization between (+)-hydantocidin and (-)-5-epi-hydantocidin were also carried out to explore some mechanistic aspects of the obtained results.

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Communication | Special issue | Vol 42, No. 2, 1996, pp. 509 - 512
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DOI: 10.3987/COM-95-S81
Syntheses of Proposed Structure of Pseudodistomin A Triacetate and Its Regioisomers on Dienyl Side-Chain

Toshiko Kiguchi, Yoko Yuumoto, Ichiya Ninomiya, and Takeaki Naito

*Kobe Pharmaceutical University, Motoyamakita, Higashinada, Kobe 658-8558, Japan


The amino alcohol (5) was employed as a common starting compound for the synthesis of the piperidines (1b), (14), and (16) with three isomeric tridecadienyl side-chains. The spectral data of the 6’E,8’Z-diene (14) are closely resembled with those of natural pseudodistomin A triacetate.

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Communication | Special issue | Vol 42, No. 2, 1996, pp. 513 - 516
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DOI: 10.3987/COM-95-S82
Novel Indole-Ring Construction Method for the Synthesis of 2-Trifluoromethylidoles

Kazuyuki Miyashita, Katsutoshi Tsuchiya, Katsunori Kondoh, Hideto Miyabe, and Takeshi Imanishi

*Faculty of Pharmaceutical Science, Osaka University, 1-6 Yamadaoka, Toyonaka, Osaka 560-0043, Japan


Novel indole-ring construction method, which is particularly effective for the synthesis of 2-perfluoroalkylindoles, and introduction of a cyanomethyl group at C-3 of 2-perfluoroalkylindoles by means of the Mannich reaction are described.

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Communication | Special issue | Vol 42, No. 2, 1996, pp. 517 - 523
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DOI: 10.3987/COM-95-S83
Novel Nonprostanoid Prostacyclin (PGI2) Mimetics with Heterocyclic Moiety

Yuuki Nagao, Kanji Takahashi, Kazuhiko Torisu, Kigen Kondo, and Nobuyuki Hamanaka

*Minase research Institute, Ono Pharmaceutical Co., Ltd., Shimamoto, Mishima, Osaka 618, Japan


Structural modification of [2-(2-benzhydryloxyiminopentyl)-1,2,3,4-tetrahydro-5-naphthyloxy]acetic acid (4), previously identified as a PGI2 agonist without a PG skeleton, was examined. Conversion of the oxime moiety in 4 to the pyrazole led to [2-(4-benzhydrylpylazoyl)methyl-1,2,3,4-tetrahydro-5-naphthyloxy]acetic acid (34) which strongly inhibited ADP-induced aggregation of human platelets in vitro.

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Communication | Special issue | Vol 42, No. 2, 1996, pp. 525 - 528
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DOI: 10.3987/COM-95-7257
A Microwave-accelerated Intramolecular Diels-Alder Reaction. Approach to Compactin

Kazuhiko Takatori, Kazushi Hasegawa, Satoshi Narai, and Masahiro Kajiwara

*Department of Medicinal Chemistry, Meiji Pharmaceutical University, 2-522-1 Noshio, Kiyose, Tokyo 204-8588, Japan


Microwave irradiation drastically accelerated the intramolecular Diels-Alder reactions of 5a-c as compared with conventional heating. The resulting carboxylic acid (7c) was converted, to the decalin unit (2a), which is a possible key intermediate for synthesis of compactin (1).

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Communication | Special issue | Vol 42, No. 2, 1996, pp. 529 - 532
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DOI: 10.3987/COM-95-S89
Versatile Synthesis of Enantiomerically Pure trans-2,5-Disubstituted Pyrrolidines

Michael Dockner, N. André Sasaki, and Pierre Potier

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


Enantiomerically pure trans-(2S,5S)-2,5-disubstituted pyrrolidine was synthesized starting from the versatile chiral synthon (R)-(8) and chiral 2,3-O-isopropylideneglycerol triflate (S)-(9).

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Communication | Special issue | Vol 42, No. 2, 1996, pp. 533 - 536
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DOI: 10.3987/COM-95-S90
Cycloaddition Reactions of Methacryloyl Isocyanate with Arylideneamines

Otohiko Tsuge, Taizo Hatta, Ryuzo Mizuguchi, Toshiyuki Kobayashi, and Ryouichi Kanzaki

*Department of Industrial Chemistry, Kumamoto Institute of Technology, 4-22-1, Ikeda, Kumamoto, 860 Japan


Arylideneamines (1) added to the acyl isocyanato moiety of methacryloyl isocyanate (MAI) to produce the corresponding [4 + 2] cycloadducts, 2H-1,3,5-oxadiazin-4(3H-ones (2). It has been clarified that even at low temperature the cycloadducts (2) partially dissociate to two original substrates, MAI and 1, in solution on the basis of VT-nmr spectroscopy.

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Communication | Special issue | Vol 42, No. 2, 1996, pp. 537 - 542
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DOI: 10.3987/COM-95-S94
Dirhodium(II) Tetrakis[3(S)-phthalimido-2-piperidinonate]: A Novel Dirhodium(II) Carboxamidate Catalyst for Asymmetric Cyclopropanation

Nobuhide Watanabe, Hideo Matsuda, Harumi Kuribayashi, and Shun-ichi Hashimoto

*Faculty of Pharmaceutical Sciences, Hokkaido University, Sapporo 060-0812, Japan


Dirhodium(II) tetrakis[3(S)-phthalimido-2-piperidinonate] catalyzes cyclopropanation of α-methylstyrene with d-menthyl diazoacetate to give d-menthyl menthyl (1S,2S)-2-methyl-2-phenylcyclopropanecarboxylate 90% de.

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Communication | Special issue | Vol 42, No. 2, 1996, pp. 543 - 547
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DOI: 10.3987/COM-95-S95
Enantioselective Allylic Alkylation and Amination Catalyzed by a Chiral P/N Ligand-Palladium Complex

Hideki Kubota and Kenji Koga

*Faculty of Pharmaceutical Sciences, University of Tokyo, Hongo, Bunkyo-ku, Tokyo 113, Japan


The phosphorus-containing C2-symmetric chiral amine ligand (3) has been found to be highly effective for enantioselective allylic substitution catalyzed by palladium complex. A high level of enantioselectivity has been achieved in the reaction of racemic 1,3-diphenyl-2-propenyl acetate with various C-nucleophiles (>95% e.e.) and N-nucleophiles (84-92% e.e.).

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Communication | Special issue | Vol 42, No. 2, 1996, pp. 549 - 553
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DOI: 10.3987/COM-95-S96
Aprotic Chloride and Bromide-promoted Alkyne-Iminium Ion Cyclizations

Yoshinori Murata and Larry E. Overman

*Department of Chemistry, University of California, Irvine, California 92717-2025, U.S.A.


The title cyclizations of 4-alkynyl- and 3-alkynyl-N-(methoxymethyl)-mines occur under milder conditions, and in the case of chloride in higher yields, than direct cyclizations of the corresponding secondary amine with formaldehyde and a halide salt.

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Paper | Special issue | Vol 42, No. 2, 1996, pp. 555 - 563
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DOI: 10.3987/COM-94-6935
Withanis somnifera - a Source of Exotic Withanolides

M. Iqbal Choudhary*, Samina Abbas, S. Arshad Jamal, and Atta-ur-Rahman*

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


Withania somnifera has yielded three new withanolides somnifericin (1),2,3-dehydrosomnifericin(2), and withaoxylactone (3).

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Paper | Special issue | Vol 42, No. 2, 1996, pp. 565 - 575
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DOI: 10.3987/COM-95-S22
Carbometalation of Cyclopropenes. Seteroselective Synthesis of Divinyl Ketones via 1,5-Hydrogen Migration Reaction of Vunylcyclopropanes

Katsumi Kubota, Masahiko Isaka, and Eiichi Nakamura

*Department of Chemistry, Tokyo Instituteof Technology, Meguro-ku, Tokyo 152-8552, Japan


Stereoselective addition of a vinyl cuprate reagent to a cyclopropenone acetal (2) followed by in situ electrophilic trapping with an alkylating agent affords a cis-1-alkyl-2-vinylcyclopropanone acetal (3), which then undergoes thermal 1,5-hydrogen migration reaction to give the acetal of a Z,E-dienone (4) in 70-90% overall yield. Hydrolysis under mild acidic conditions affords the corresponding dienone or trienone (5) in high yield.

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Paper | Special issue | Vol 42, No. 2, 1996, pp. 577 - 588
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DOI: 10.3987/COM-95-S32
Synthetic Studies of Novel 5-Azacarbapenems

Kuniyuki Oda, Takao Nakano, Hiroshi Morimoto, and Norio Takamura

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


1,2-Diazetidiiones were prepared from (2R, 3R)-epoxybutanoic acid via acidic one-pot deprotection-cyclization reaction and converted to the novel 5-azacarbapenams by an intramolecular Michael cyclization reaction.

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Paper | Special issue | Vol 42, No. 2, 1996, pp. 589 - 596
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DOI: 10.3987/COM-95-S48
Neighboring Assistance of a Hydroxyl Group on Manganese Dioxide Oxidation of Benzyl Alcohols to Lactones

Katsuya Endo, Hiroyasu Takahashi, and Minako Aihara

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


o-Hydroxymethylbenzyl alcohol and o-hydroxyethylbenzyl alcohols have been converted to phthalide and dihydroisocoumarins, very easily and in high yields, by oxidation with non-activated manganese dioxide. In contrast, the reaction of o-hydroxypropylbenzyl alcohol stopped at the aldehyde level, and afforded only a small amount of the corresponding lactone under the same condition. This implies that the first oxidation product, a benzaldehyde, could be oxidized further via a hemiacetal, but the second oxidation to lactone is very much dependent on the ability of stable intramolecular hemiacetal formation, and not on the intermolecular mode at all.

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Paper | Special issue | Vol 42, No. 2, 1996, pp. 597 - 615
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DOI: 10.3987/COM-95-S51
New Synthesis of Quinoxaline Derivatives Based on Palladium Catalyzed Oligomerization of 1,2-Diisocyanoarenes

Yoshihiko Ito, Yutaka Kojima, Michinori Suginome, and Masahiro Murakami

*Departmene of Synthetic Chemistry and Biological Chemistry, Faculty of Engineering, Kyoto University, Yoshida, Sakyou-ku, Kyoto 606-8501, Japan


Various 2,3-disubstituted quinoxaline derivatives were synthesized from monomeric and oligomeric (3-substituted quinoxaline-2-yl)palladium(ll)s, which were prepared by the reaction of o-diisocyanoarenes with trans-bromo(methyl)bis(phosphine)palladium(ll).

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Paper | Special issue | Vol 42, No. 2, 1996, pp. 617 - 624
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DOI: 10.3987/COM-95-S52
Hydrolysis of Isomeric Tricyclic Orthoesters and AM1 Molecular Modelling of the Reaction Pathway Further Evidence for Stereoselectronic Control

Pierre Deslongchamps, Yves L. Dory, and Shigui Li

*Department of Chemistry, Faculty of Sciences, Universite de Sherbrooke, Sherbrooke, Quebec, J1K 2R1, Canada


Two tricyclic orthoesters and three other onhoesters have been submitted to acid hydrolysis conditions to yield mixtures of lactones and esters. The ratios of different products have been rationalized in terms of stereoelectronic, steric and entropy effects at the various steps. A quantitative AM1 investigation has been carried out, starting from the only tricyclic hemi-orthoester intermediate of the whole system, in order to compare the hydrolysis routes leading to the kinetic and thermodynamic lactone products.

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Paper | Special issue | Vol 42, No. 2, 1996, pp. 625 - 634
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DOI: 10.3987/COM-95-S54
tert-Butylcyclopentane Derivatives. Part 8. Synthesis of tert-Butylcyclopentane-fused Pyrimidin-4-ones

Zsolt Szakonyi, Ferenc Fülöp, Gábor Bernáth, and Pál Sohár

*Institute of Pharmaceutical Chemistry, Albert Szent-Györgyi Medical University, H-6701 Szeged, Eötv¨øs u.6., Hungary


In the reactions of ethyl (1R*,2S*,4S*)-2-amino-4-tert-butyl-1-cyclopentanecarboxylate (4) or (1R*,3S*,5S*)-3-tert-butyl-6-azabicyclo[3.2.0]heptan-7-one (2) or (1R*,2S*,4S*)-2-amino-4-tert-butyl-1-cyclopentanecarboxamide (6) with imidates or triethyl orthobenzoate, tert-butylcyclopentane-fused dihydropyrimidin-4-ones (7a-e) were prepared. The azetidinone (2) with lactim ethers furnished pyrrolo-, pyrido- and azepino[1,2-a]pyrimidin-4-ones (8-10) in ringenlargement reactions. Ethyl (1R*,2S*,4S*)-2-amino-4-tert-butyl-1-cyclopentanecarboxylate (4) and ethyl (1R*,2S*,4S*)-2-benzylamino-4-tert-butyl-1-cyclopentanecarboxylate (5) and potassium cyanate or phenyl isocyanate or potassium thiocyanate or phenyl isothiocyanate, yielded pyrimidine-2,4-diones or 2-thioxopyrimidin-4-ones (11-22).

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Paper | Special issue | Vol 42, No. 2, 1996, pp. 635 - 643
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DOI: 10.3987/COM-95-S59
Tandem Stereoselective Conjugate Additions to α,β-Unsaturated Oxazolines

Nathalie Dahuron, Nicole Langlois, Angèle Chiaroni, and Claude Riche

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


Tandem stereoselective conjugate additions to two molecules of activated α,β-unsaturated oxazolines have led to substituted 2,4-bis-(4-phenyl-4,5-dihydrooxazol-2-yl)-cyclopent-1-enylamines.Their general structure was deduced from spectral data and confirmed by X-ray analysis.

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Paper | Special issue | Vol 42, No. 2, 1996, pp. 645 - 651
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DOI: 10.3987/COM-95-S61
Synthesis and Biological Evaluation of Sodium 2β-[(2,5-Dihydro-6-hydroxy-2-methyl-5-oxo-1,2,4-triazin-3-yl)sulfonylmethyl]-2α-methylpenam-3α-carboxylate 1,1-Dioxide

Eduardo L. Setti, Oludotun A. Phillips, Andhe V. N. Reddy, Chieko Kunugita, Akio Hyodo, Ronald G. Micetich, and Samarendra N. Maiti

*SynPhar Laboratories Inc., 4290-91A Street, Edmonton, Alberta, T6E 5V2, Canada


A new β-lactamase inhibitor, sodium 2β-[(2,5-dihydro-6-hydroxy-2-methyl-5-oxo-1,2,4-triazin-3-yl)sulfonymethyl]-2α-methylpenam-3α-carboxylate 1,1-dioxide (3). was synthesized. The compound (3) had excellent invitro inhibitory activity except against cephalosporinase. In combination with ampicillin, piperacillin and ceftazidime, its synergistic effects was inferior to tazobactam, thus suggesting poor penetration through the bacterial cell wall.

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Paper | Special issue | Vol 42, No. 2, 1996, pp. 653 - 668
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DOI: 10.3987/COM-95-S62
β-Lactamase Inhibitors: Synthesis and in vitro Evaluation of 6-[(1-Substituted1,2,3-Triazol-4-yl)methylene]penicillanic Acid Sulfones

Paul Eby, Maxwell D. Cummings, Oludotun A. Phillips, David P. Czajkowski, Maya P. Singh, Paul Spevak, Ronald G. Micetich, and Samarendra N. Maiti

*SynPhar Laboratories Inc., 4290-91A Street, Edmonton, Alberta, T6E 5V2, Canada


A series of 6-[(1-substituted 1,2,3-triazol-4-yl)methylene]penicillani acid sulfones were synthesized and tested for β-lactamase inhibitory activity. The (6Z)-isomers were over 100 times more potent than the (6E)-isomers against cell-free β-lactamases and were synergistic with ampicillin against a variety of β-lactamase producing bacteria.

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Paper | Special issue | Vol 42, No. 2, 1996, pp. 669 - 676
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DOI: 10.3987/COM-95-S68
De Novo Synthesis of Racemic Altronolactam and Arabinonolactam Azasugars

Théophile Tschamber, Elsa-Maria Rodriguez-Perez, Patrick Wolf, and Jacques Streith

*Ecole Nationale Supérieure de Chimie de Mulhouse, Université de Haute Alsace, 3, Rue Alfred Werner 68093 Mulhouse Cedez, France


Starting from the known peracetylated piperidinose derivatives (7a) and (7b), the corresponding altrono- and arabinon- lactams (4) and (5) were obtained in a straightforward way. A selective two-step hydrolysis of the anomeric acetoxy groups gave the free hydroxyls (8a) and (8b) which were oxidised to the β-lactams (9a) and (9b), respectively. Deprotection of these latter compounds led to the target molecules.

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Paper | Special issue | Vol 42, No. 2, 1996, pp. 677 - 689
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DOI: 10.3987/COM-95-S73
Diels-Alder Reaction of the Dihydropyridinones V: Approach to the Ircinal B Core

Yasuhiro Torisawa, Mohamed Ayman Ali, Fabrice Tavet, Akiko Kageyama, Maki Aikawa, Naoko Fukui, Tohru Hino, and Masako Nakagawa*

*Faculty of Pharmaceutical Sciences, Chiba University, 1-33 Yayoi-cho, Inage-ku, Chiba 263-8522, Japan


Thermal and high-pressure Diels-Alder reaction of the suitably assembled dihydropyridinones afforded the hydroisoquinoline derivatives, which were transformed to the key intermediates for the ABC substructure of ircinal B.

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Paper | Special issue | Vol 42, No. 2, 1996, pp. 691 - 699
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DOI: 10.3987/COM-95-S75
Synthesis of Fused Pyrimidinones by Reaction of Aminoarenecarboxamide with Esters; Preparation of Pyrrolo[2,3-d]-, Thieno[2,3-d]-, Isoxazolo[5,4-d]-, and 1,2,3-Triazolo[4,5-d]-pyrimidinones, and Quinazolones

Akira Miyashita, Katsuhiro Fujimoto, Tomomi Okada, and Takeo Higashino

*Schol of Pharmaceutical Sciences, University of Shizuoka, 52-1 Yada, Shizuoka 422-8526, Japan


Several fused pyrimidinones were synthesized by reaction of aminoarenecarboxamide with esters in moderate to good yields. In the presence of sodium ethoxide, treatments of 2-amino-1-phenyl-3-pyrrolecarboxamide(4,5, and 6), 2-amino-3-thiophenecarboxamide (14), 3-amino-4-isoxazolecarboxamide (10 and 11), 4-amino-1,2,3-triazole-5-carboxamide (16), and o-aminobenzamide (18) with esters (3) such as ethyl formate (3a) and ethyl acetate (3b) led to the corresponding pyrrolo[2,3-d]- (7,8, and 9), and thieno[2,3-d]pyrimidin-4(3H)-ones (15), isoxazolo[5,4-d]pyrimidin-4(5H)-ones (12 and 13), 1,2,3-triazolo[4,5-d]pyrimidin-7(6H)-ones (17), and 4(3H)-quinazolones (19), respectively.

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Paper | Special issue | Vol 42, No. 2, 1996, pp. 701 - 722
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DOI: 10.3987/COM-95-S76
Ring Opening of Optically Active cis-Disubstituted Aziridino Alcohols: An Enantiodivergent Synthesis of Functionalized Amino Alcohol Derivatives

Kaoru Fuji, Takeo Kawabata, Yoshimitsu Kiryu, and Yukio Sugiura

*Institute for Chemistry, Kyoto University, Uji, Kyoto 611-0011, Japan


Ring-opening reactions of optically active cis-disuhstituted aziridino alcohols have been investigated. Regio- and stereo-selective ring opening took place with internal and external nucleophiles. Unusual amino acids derivatives (14) and (15), the key synthetic intermediates for bestatin and related peptides, have been prepared.

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46 data found. 1 - 30 listed Next Last