Regular Issue

Vol. 29, No. 3, 1989

22 data found. 1 - 22 listed
Communication | Regular issue | Vol 29, No. 3, 1989, pp. 411 - 414
Published online:
DOI: 10.3987/COM-89-4796
Peperomins A, B, and C, Novel Secolignans from Peperomia japonica

Chiu-Ming Chen,* Feng-Yih Jan, Ming-Tyan Chen, and Tsong-Jen Lee

*Department of Chemistry, National Tsing Hua University, Hsinchu, Taiwan 30013, Taiwan, R.O.C.


Three novel lignans having unusual seco structure, peperomins A, B and C were isolated from the fresh whole plant of Peperomia japonica Makino (Piperaceae). The structures of peperomins A, B and C were established as I, II and III, respectively, on the basis of spectroscopic and crystallographic evidence.

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Communication | Regular issue | Vol 29, No. 3, 1989, pp. 415 - 418
Published online:
DOI: 10.3987/COM-89-4803
A Convenient Reductive Cyclisation of 2-Nitro-β-nitrostyrenes to Indoles

Sundramoorthi Rajeswari, Kevin J. Drost, and Michael P. Cava*

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


A simple synthesis of a variety of 2,3-unsubstituted indoles containing alkoxy and acetoxy groups has been developed. This method involves the reductive cyclisation of 2,β-dinitrostyrenes with ammonium formate in the presence of a catalytic amount of Pd/C in refluxing methanol, and affords indoles in good to excellent yields.

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Communication | Regular issue | Vol 29, No. 3, 1989, pp. 419 - 426
Published online:
DOI: 10.3987/COM-89-4804
Glycosylaziridine Derivatives

Jean M. J. Tronchet* and Mohamed A. M. Massoud

*Institute of Pharmaceutical Chemistry, University of Geneva, 30, Quai e.-Ansermet, CH-1211 Geneva 4, Switzerland


Addition of ammonia to the bromoenoses Ia-e afforded the corresponding secondary dissymmetric aziridines IIa-e respectively. The stereochemistry of their ring opening and ring expansion to δ2-oxazolines has been studied and the absolute configuration of the two newly obtained asymmetric carbon atoms was established.

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Communication | Regular issue | Vol 29, No. 3, 1989, pp. 427 - 430
Published online:
DOI: 10.3987/COM-89-4827
An Efficient Total Synthesis of AC-5-1: Novel 5-Lipoxygenase Inhibitor Isolated from Artocarpus communis

Jun Nakano,* Katsuhiro Uchida, and Yasuo Fujimoto

*Kyoto Research Institute, Kaken Pharmaceutical Co., Ltd., Shinomiya, Minamikawara-cho, Yamashina-ku, Kyoto 607-8042, Japan


The first total synthesis of the highly potent 5-lipoxygenase inhibitor, AC-5-1, from Artocarpus communis has been accomplished by using the oxazoline method of Meyers as a key step.

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Communication | Regular issue | Vol 29, No. 3, 1989, pp. 431 - 434
Published online:
DOI: 10.3987/COM-89-4828
Study on the Structure of Pseudocrown Ether Formed in the Reaction of Ionophore 6-O-BPY1 and Cu+ by 500 MHz 1H Nmr Spectrometry

Tatsuya Nabeshima, Tadashi Inaba, and Naomichi Furukawa*

*Department of Chemistry, University of Tsukuba, 1-1-1 Ten-nodai, Tsukuba-shi, Ibaraki, 305-8571, Japan


The structures of ionophore 6-O-bpy 1 and 1-Cu+ complex were studied by 500 MHz 1H nmr spectrometry. Characteristic downfield and upfield shifts of the aromatic
protons, and the methyl and the methylene protons in the picolyl moiety support strongly generation of pseudocrown structure in the 1-Cu+ complex.

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Communication | Regular issue | Vol 29, No. 3, 1989, pp. 435 - 440
Published online:
DOI: 10.3987/COM-89-4829
Synthesis of 2,2-Disubstituted Succinimides and Their Regioselective Thiocarbonylation Reaction

Yoshiyuki Kosugi,* Masako Kosugi, and Fumiko Hamaguchi

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


2,2-Dialkoxy- and 2,2-bis(alkylthio)succinimide (3a-c and 3g) were prepared from 2,3-dibromosuccinimide by the reaction with alkoxide or thiolate anion. In contrast to most 2,2-disubstituted succinimides, thiocarbonylation reaction of the imides bearing ethylenedioxy group with Lawesson reagent occurred at the more hindered carbonyl group to give monothioimides (6c and 6d) as major products.

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Communication | Regular issue | Vol 29, No. 3, 1989, pp. 441 - 444
Published online:
DOI: 10.3987/COM-89-4852
Synthesis, Crystal Structure, and Conformational Property of N, N’-Dimethyl-1,11-(methanoaminomehtano)-5H,7H-dibenzo[b,g][1,5]-thiazocine: a New Heterocyclic system

Hisashi Fujihara, Nobuo Oi, Ryouichi Akaishi, Takatoshi Kawao, and Naomichi Furukawa*

*Department of Chemistry, University of Tsukuba, 1-1-1 Ten-nodai, Tsukuba-shi, Ibaraki, 305-8571, Japan


A new heterocyclic compound, N,N’-dimethyl-1,11-(methanoaminomethano)-5H,7H-dibenzo[b,g][1,5]thiazocine has been synthesized; the eight-membered ring is in the rigid chair-chair conformation.

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Communication | Regular issue | Vol 29, No. 3, 1989, pp. 445 - 448
Published online:
DOI: 10.3987/COM-89-4848
Enantiocontrolled Approach to Natural Products Utilizing (S)-O-Benzylglycidol as Common Chiral Precursor

Seiichi Takano,* Yoshinori Sekiguchi, and Kunio Ogasawara

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


An enantiocontrolled route to the aggregation pheromone of European elm bark beetle (12), the sex pheromone of cigarette beetle serricornin (15), and the spiroketal segment (24) of the sixteen-membered macrolide antibiotics milbemycins and avermectins is described using the intermediates derived from (S)-O-benzylglycidol (1) as common chiral precursor.

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Communication | Regular issue | Vol 29, No. 3, 1989, pp. 449 - 452
Published online:
DOI: 10.3987/COM-89-4868
Enantioselective Synthesis of 2,2-Disubstituted 3-Cyclopentenone from 3-Alkyl-4-thianones

Haruo Matsuyama,* Yoshihiro Ebisawa, Michio Kobayashi, and Nobumasa Kamigata

*Department of Chemistry, Faculty of Science, Tokyo Metropolitan University, Hachioji, Tokyo 192-0397, Japan


Enantioselective Synthesis of quaternary carbon centers through Michael-type alkylation of chiral imines of 3-methyl-4-thianone and successive regioselective synthesis of chiral 2,2-dialkyl-3-cyclopentenone via Ramberg-Bäcklund reactions are reported.

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Communication | Regular issue | Vol 29, No. 3, 1989, pp. 453 - 458
Published online:
DOI: 10.3987/COM-89-4884
α-Allylation of β-Tetronic Acids and Chirality Transfer via the 4-Oxygenated 2(5H)-Furanone System

Takefumi Momose,* Naoki Toyooka, Hiromi Fujii, and Hironobu Yanagino

*Faculty of Pharmaceutical Sciences, Kinki University, 3-4-1, Kowakae, Higashi-Osaka 577-8502, Japan


α-Allylation of the β-tetronate system was accomplished by direct attack of allyl halide on C-3 of the system in the presence of potassium carbonate in N,N-dimethylformamide or the Claisen rearrangement of allyl tetronates concomitantly formed in the preceding direct allylation. The chirality of natural L- amino acids was transferred into the β-tetronic acid system at the α-position via initial incorporation into the γ-position and subsequent α-allylation by application of analogous sequence of reactions.

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Communication | Regular issue | Vol 29, No. 3, 1989, pp. 459 - 462
Published online:
DOI: 10.3987/COM-89-4892
Intramolecular Cyclization of Methylthiofuropyridones

Takeaki Naito,* Okiko Miyata, and Ichiya Ninomiya

*Kobe Women’s College of Pharmacy, Motoyamakita, Higashinad, Kobe, Hyogo 658, Japan


Methylthiofuropyridone 4 has been proved as a potential synthon for the construction of indoloquinolizidine structure by the intramolecular cyclization involving methylthio and lactam carbanyl groups.

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Paper | Regular issue | Vol 29, No. 3, 1989, pp. 463 - 475
Published online:
DOI: 10.3987/COM-89-4768
Azafluorene and Aporphine Alkyloids from Polyalthia longifolia

Yang-Chang Wu*

*School of Pharmacy, Kaohsiung Medical College, 100 Shih Chuen 1st Rd., Kaohsiung 80708, Taiwan, R.O.C.


A novel azafluorene alkaloid, polylongine (5-hydroxy-6-methoxy-1-methyl-4-azafluoren-9-ol) (1) and three new aporphine N-oxide alkaloids named (+)-O-methylbulbocapnine β-N-oxide (2), (+)-O-methylbulbocapnine-α-N-oxide (3) and (+)-N-methylnandigerine-β-N-oxide (4) were isolated from the leaves of Polyalthia longifolia (Sonn.) Thwaites (Annonaceae).

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Paper | Regular issue | Vol 29, No. 3, 1989, pp. 477 - 484
Published online:
DOI: 10.3987/COM-89-4787
Synthesis of (±)-(2R*,11bS*)-3’-Aryl-9,10-dimethoxy-1,3,4,5,7,11b-hexahydrospiro[benzo[a]quinolizin-2,5’-oxazolidine]-2’,4’-diones

J. Carlos Menéndez, Carmen Avendaño, and Mónica M. Söllhuber*

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


The synthesis of (±)-(2R*,11bS*)-3’-aryl-9,10-dimethoxy-1,3,4,6,7,11b-hexahydrospiro[benzo[α] quinolizin-2,5’-oxazolidine]-2’,4’-diones (1) was achieved by two alternative routes involving the treatment of cyanohydrin 3 with aryl isocyanates via 4-imino derivatives 5 and 6 or the cyclization of the hydroxy ester 9 with aryl isocyanates. Compounds 1 present a trans Conformation in the quinolizidine system and exist in a (2R*,11bS*) configuration.

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Paper | Regular issue | Vol 29, No. 3, 1989, pp. 485 - 496
Published online:
DOI: 10.3987/COM-89-4802
The Reaction of 2-Chiloro-10-N-methylphenothiazine with Aromatic Nitriles and Lithium Dialkylamides in THF: Synthesis Structure of 1-Cyano-2-(3’,4’,5’-trimethoxybenzyl)-10-N-methylphenothiazine

Edward R. Biehl,* Subhash P. Khanapure, Upali Siriwardane, and Matt Tschantz

*Department of Chemistry, Southern Methodist University, P.O. Box 750314, Dallas, TX 75275-0314, U.S.A.


10-N-Methyl-1,2-didehydrophenothiazine (2), generated in situ from 10-N-methyl-2-chlorophenothiazine (1), reacts via the tandem addition-rearrangement aryne (TARA) mechanism with lilhio-arylacetonitriles yielding rearranged products (3a-c), after proton quench. The X-ray structure of title compound 3a demonstrates conclusively that the initial nitrile anion addition step in the TARA reaction occurs at the 2-position of 2. In previous studies of nucieophilic additions to 2, this regioselsctivity had only been assumed on the basis of the well-documented strong meta-directing effect of the lo-nitrogen atom.

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Paper | Regular issue | Vol 29, No. 3, 1989, pp. 497 - 509
Published online:
DOI: 10.3987/COM-89-4808
An Imprived Synthesis of 2-Carbamoyloxymethyl-1,4-dihydropyridine

Kunio Suzuki,* Ryosuke Ushijima, Tetsuji Myiano, and Susumu Nakagawa

*Okazaki Research Laboratories, Banyu Pharmaceutical Co., Ltd., 3-9-1, Kamimutuna, Okazaki, Aichi 444, Japan


A new synthesis of 3-amino-4-carbamoyloxybutenoic esters by conjugate addition of ammonia to 4-carbamoyloxy-2-butynoic esters is reported. Numerous dihydropyridines were prepared from the resulting 3-aminobutenoates by condensation with benzylideneacetoacetates.

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Paper | Regular issue | Vol 29, No. 3, 1989, pp. 511 - 520
Published online:
DOI: 10.3987/COM-89-4819
Photochemistry of 5-(2-Acetoxyaryl)-2(3H)-furanones. 2. Isolation of Chromome-3-acetic Acids and Their Photodecarboxylation to 3-Methychromones

Luis Fillol, Roberto Martínez-Utrilla, Miguel A. Miranda,* and Isabel M. Morera

*Departamento de Química Oránica, Facultad de Farmacia, Av. Blasco Ibañez 13, 46010 Valencia, Spain


Irradiation of the enol lactones 1a,b in methanol led to the vinyl ketones 2a,b and the chromones 3a,b, while irradiation in benzene gave the vinyl ketones 2a,b and the chromones 4a,b and 5a,b. The photodecarboxylatian of 4a,b to 5a,b, analogous to that of phisnylacetic acid, is very efficient. The mechanistic implications of these observations are discussed.

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Paper | Regular issue | Vol 29, No. 3, 1989, pp. 521 - 527
Published online:
DOI: 10.3987/COM-89-4834
Studies of the Chemical Constitutions of the Seeds of Peganum harmala; Isolation and Structure Elucidation of Two β-Carbolines — Harmalacine and Norharmine

Salimuzzaman Siddiqui,* Obaid Yusuf Khan, Shaheen Faizi, and Bina Shaheen Siddiqui

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


A new tetracyclic β-carboline, harmalacinine, has been isolated from the seeds of Peganum harmala, along with norharmine, and their structures elucidated as I and II respectively through spectral studies.

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Paper | Regular issue | Vol 29, No. 3, 1989, pp. 529 - 537
Published online:
DOI: 10.3987/COM-89-4839
Studies in the Formation of Oxidoles from Their Indolozabicyclo[3.3.1]nonane Counterparts and Implications for the Biogenesis of Alstonisine

Sean P. Hollinshead, Desirée S. Grubisha, Dennis W. Bennett, and James M. Cook*

*Department of Chemistry, University of Wisconsin-Milwaukee, Milwaukee, Wisconsin 53201, U.S.A.


Treatment of the Na-H indoloazabicyclo[3.3.1]nonane 5 with t-BuOCl and hydrolysis of the intermediate chloroindolenine provided the oxindole 6 in 88% yield. In contrast, Na-methyl analogues 9a-c failed to rearrange to the corresponding oxindoles when reacted under the analogous conditions. Instead, the indolooctane-1,4-dione 11 and an isomer related to 12 were isolated from the oxidation of 9a. The implications in regard to the biogenesis of alstonisine 2 are discussed.

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Paper | Regular issue | Vol 29, No. 3, 1989, pp. 539 - 545
Published online:
DOI: 10.3987/COM-89-4846
A Facile Synthesis of 2-Aryl- and 2-Heteroaryl-substituted 4-Aminoquinolines

Lucjan Strekowski,* Suk-Bin Kong, Marek T. Cegla, and Donald B. Harden

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


Schiff’s bases, obtained from 2-aminobenzonitrile and aryl or heteroaryl methyl ketones, are lithiated with lithium diisopropylamide at the methyl group. The intermediate carbanions undergo cyciization to a quinoline system in a high yield. The corresponding Schiff’s base obtained from propiophenone undergoes an unusual addition reaction with the lithium reagent instead.

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Paper | Regular issue | Vol 29, No. 3, 1989, pp. 547 - 555
Published online:
DOI: 10.3987/COM-89-4858
Formation of Regioisomeric Tetrahydroisoxazolo[2,3-d][1,4]benzodiazepines by Kinetic and Thermodynamic Controls

Irina Merenda, Rosaria Ottanà, Giovanni Romeo,* and Enrico Rotondo

*Università di Messina, Viale Annunziata, 98168 Messina, Italy


1,3-Dipolar cycloaddition of 1,4-benzodiazepine N-oxide with acrylic esters produces annelated 4- and 5-substituted isoxazolidines. 4-Substituted regioisomers are unstable at higher reaction temperatures and rearrange pIesumably via a 1,3-dipolar cycloreversion to regenerate 5-substituted derivatives. structure and stereochemistry of cycloadducts have been assigned by means of 1H nmr spectroscopy assisted by NOE measurements. The experienced regiochemistry has been rationalized according to the electron-rich nature of benzodiazepine nitrones.

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Review | Regular issue | Vol 29, No. 3, 1989, pp. 557 - 595
Published online:
DOI: 10.3987/REV-89-386
N-Substituted Pyridinium Salts

Wanda Sliwa* and Barbara Mianowska

*Institute of Chemistry and Environmental Protection, Pedagogical University, Al. Armii Krajowej 13/15, 42-201 Czestochowa, Poland


N-Substituted pyridinium salts are presented in view of their syntheses, reactivity and physicochemical properties, along with their biological activities and applications.

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Review | Regular issue | Vol 29, No. 3, 1989, pp. 597 - 627
Published online:
DOI: 10.3987/REV-89-398
Heterocyclic Sonochemistry

Yu. Goldberg, R. Strukovich, and E. Lukevics*

*Latvian Institute of Organic Synthesis, Aizkraukles 21, Riga, LV-1006, Latvia


Sonochemical reactions involving heterocyclic compounds are surveyed. Major synthetic applications of sonolysis in the chemistry of heterocyclic compounds are described.

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22 data found. 1 - 22 listed