Regular Issue

Vol. 29, No. 8, 1989

26 data found. 1 - 26 listed
Communication | Regular issue | Vol 29, No. 8, 1989, pp. 1435 - 1438
Published online:
DOI: 10.3987/COM-89-4987
Normavacurine and Minfiensine, Two New Alkaloids with C19H22N2O Formula from Strychnos Species

Georges Massiot,* Philippe Thépenier, Marie-José Jacquier, Louisette Le Men-Olivier, and Clément Delaude

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


Minfiensine and normavacurine are two novel C19H22N2O alkaloids from Strychons minfiensis, S. potatorum and S. longicaudata. Minfiensine is characterized by a N-1 - C-3 bond instead of the usual N-1 - C-2 bond.

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Communication | Regular issue | Vol 29, No. 8, 1989, pp. 1439 - 1441
Published online:
DOI: 10.3987/COM-89-4997
An Alternative Model for the Biogenesis of Xanthanolides

Antonio G. González, Antonio Galindo,* María del Mar Afonso, amd Horacio Mansilla

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


Hydroperoxide transposition of 4-hydroperoxyguaianolide (10) afforded xanthanolide (12). The possible biogenetic implications of this process are discussed.

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Communication | Regular issue | Vol 29, No. 8, 1989, pp. 1443 - 1446
Published online:
DOI: 10.3987/COM-89-4996
Reaction of 6-Methyl-2-phenyl-4H-1,3-oxazin-4-one with Oxime Dianions

Yutaka Yamamoto,* Yasuo Morita, Reiko Kikuchi, Emiko Yokoo, Kaori Ohtsuka, and Miwako Katoh

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


6-Methyl-2-phenyl-4H-1,3-oxazin-4-one (1) undergoes novel ring transformation upon treatment with oxime dianions to give isoxazoles (3a-d) and pyridine N-oxides (4c-f). The reaction of 1 with cycloheptanone oxime (2a) or cyclododecanone oxime (2b) in the presence of two equivalents of butyllithium affords isoxazole (3a or 3b). With acetophenone oxime (2c) or acetoxime (2d), pyridine N-oxide (4c or 4d) is formed as a minor product in addition to isoxazole (3c or 3d). Treatment with cyclopentanone oxime (2e) or cyclohexanone oxime (2f) yields pyridine N-oxides (4e or 4f) as a sole product.

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Communication | Regular issue | Vol 29, No. 8, 1989, pp. 1447 - 1453
Published online:
DOI: 10.3987/COM-89-5019
Artonins A and B, Two New Prenylflavonoes from the Root Bark of Artocarpus heterophyllus Lamk

Yoshion Hano, Miwa Aida, Mikako Shiina, Taro Nomura,* Takatoshi Kawai, Hiroshi Ohe, and Kengo Kagei

*Faculty of Pharmaceutical Sciences, Toho University, 2-2-1, Miyama, Funabashi, Chiba 274-8510, Japan


Two new prenylflavones, artonins A (1) and B (2), were isolated from the root bark of Artocarpus heterophyllus Lamk. (Moraceae), along with two known prenylflavones, heterophyllin (3) and cycloheterophyllin (4). The structures of artonins A and B were shown to be 1 and 2, respectively, on the basis of the X-ray crystallographic analysis, spectroscopic data, and chemical evidence.

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Communication | Regular issue | Vol 29, No. 8, 1989, pp. 1455 - 1458
Published online:
DOI: 10.3987/COM-89-5028
Synthesis and Reaction of 3-Hydroxyenamides

Shunsaku Ohta,* Motoshige Sumino, Tsutomu Sasaki, and Nobuyuki Yamagami

*Kyoto Pharmaceutical University, Misasagi, Yamashina-ku, Kyoto 607-8412, Japan


3-Hydroxyenamides (7) were prepared starting from 1,3-dicarbonyl compounds (4), and the enamides (7) readily reacted with π nucleophiles in the presence of trifluoroacetic anhydride to give 3-arylketones (11) in moderate yields.

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Communication | Regular issue | Vol 29, No. 8, 1989, pp. 1459 - 1464
Published online:
DOI: 10.3987/COM-89-5034
Polyannulated Tropylium Compounds Having Benzothiazine and Related Heterocyclic Rings. Formation of o- and p-Benzoquinonoid Products by Rearrangement

Tetsuo Nozoe,* Kimio Shindo,* Hidetsugu Wakabayashi, and Sumio Ishikawa

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


Tropylium compounds having tri-annulated heterocycles (11 and 15) are obtained by the reaction of 2,4-dibromo-7-methoxy- and 3,5,7-tribromo-2-methoxytropone with O-aminophenol and O-aminobenzenethiol, via di-annulated compounds. Rearrangements to di- and tri-annulated o- and p-benzoquinonoid compounds (13, 16 and 20) take place during the attempted synthesis of some tri-annulated tropylium systems. Possible pathways for these reactions are discussed.

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Communication | Regular issue | Vol 29, No. 8, 1989, pp. 1465 - 1468
Published online:
DOI: 10.3987/COM-89-5052
Structure and Stereochemistry of Emargiatine-A, a Novel Cytotoxic Sesquiterpene Pyridine Alkaloid from Maytenus emarginata: X-Ray Crystal Steructure of Emarginatine-A Monohydrate

Yao-Haur Kuo, Chung-Hsiung Chen, Li-Ming Yang Kuo, Ming-Lu King, Tian-Shung Wu, Sheng-Teh Lu, Ih-Sheng Chen, Donald R. McPhail, Andrew T. McPhail,* and Kuo-Hsiung Lee*

*Division of Medicinal Chemistry and Natural Products, School of Pharmacy, University of North Carolina, Chapel Hill, North Carolina 27599-7360, U.S.A.


The structure and stereochemistry of emarginatine-A (1), a novel cytotoxic sesquiterpene pyridine alkaloid isolated from Maytenus emarginata, have been established from spectral data in conjunction with a single-crystal X-ray analysis of its monohydrate.

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Communication | Regular issue | Vol 29, No. 8, 1989, pp. 1469 - 1472
Published online:
DOI: 10.3987/COM-89-5057
Synthesis of (+)-1-Deoxynojirimycin from (S)-Pyroglutamic Acid

Nobuo Ikota*

*National Institute of Radiological Sciences, 9-1, Anagawa-4-Chome, Inage-ku, Chiba 263-0024, Japan


The synthesis of (+)-1-deoxynojirimycin (10) has been achieved from (S)-pyroglutamic acid by cis hydroxylation of the trans-α,β-unsaturated ester 2 and reduction of the enone 5b as the key reactions. 5-O-Carbamoylpolyoxamic acid (14) and (+)-1-deoxymannojirimycin (11) were also synthesized from 4b and 7b, obtained by the above reactions as the minor diastereomer, respectively.

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Communication | Regular issue | Vol 29, No. 8, 1989, pp. 1473 - 1476
Published online:
DOI: 10.3987/COM-89-5064
A Concise Enantioselective Synthesis of Acromelic Acid B from (S)-O-Benzylglycidol

Seiichi Takano,* Shun’ichi Tomita, Yoshiharu Iwabuchi, and Kunio Ogasawara

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


The potent neurotoxin, acromelic acid B, has been synthesized by an enantioselective route employing an intramolecular 1,3-dipolar cyclization as the key step.

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Paper | Regular issue | Vol 29, No. 8, 1989, pp. 1477 - 1487
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DOI: 10.3987/COM-89-4933
Syntheses of Functionalized Derivatives of Quinazolines and 1,4-Bensodiazepines

Maurizio Anzini, Antonio Garofalo, and Salvatore Vomero*

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


The 2-substituted 1,4-benzodiazepines (4 and 6) were synthesized. The reaction of 2-aminobenzophenone oximes with ethyl 4-chloroacetoacetate gave the 1,4-benzodiazepines (4) and the 1,2-dihydroquinazolines (5); the latter were treated with a base to result ring expansion giving the 1,4-benzodiazepines (6).

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Paper | Regular issue | Vol 29, No. 8, 1989, pp. 1489 - 1495
Published online:
DOI: 10.3987/COM-89-4944
Three New Clerodane-type Diterpenoids, Clerodinin C, Clerodinin D and Clerodiol, from Clerodendron brachyanthum Schauer

Yun-Lian Lin, Yueh-Hsiung Kuo,* and Yuh-Lin Chen

*Department of Chemistry, National Taiwan University, Roosevelt Road Section 4, Taipei 106, Taiwan, R.O.C.


Clerodinin C, clerodinin D and clerodiol, three new clerodane-type diterpenoids have been isolated from the hexane extract of the leaves of Clerodendron brachyanthum Schauer. Their structures have been elucidated by means of spectroscopic and chemical evidence.

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Paper | Regular issue | Vol 29, No. 8, 1989, pp. 1497 - 1516
Published online:
DOI: 10.3987/COM-89-4947
Design and Synthesis of 4-Oxoquinolin-2-yl-6-heptenoic Acid Derivatives as HMG-CoA Reductase Inhibitors

Gary M. Coppola,* Terrence J. Scallen, Ann DelPrete, and Rita Montano

*Sandoz Research Institute, Sandoz, Inc., Route 10, East Hanover, New Jersey 07936, U.S.A.


Syntheses of two isomeric series of 4-oxoquinolin-2-yl-6-heptenoic acid derivatives 7 and 8 are described. The quinolinone portion of the molecules was constructed from the reaction of either an N-alkyl- or N-arylisatoic anhydride with an appropriate ketone enolate. The side-chain was elaborated by way of an aldol condensation using ethyl acetoacetate dianion fllowed by stereoselective ketone reduction. The N-aryl series 8 exhibited significantly greater inhibitory activity than the N-alkyl series 7.

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Paper | Regular issue | Vol 29, No. 8, 1989, pp. 1517 - 1528
Published online:
DOI: 10.3987/COM-89-4984
Synthesis and Cardiotonic Activity of 5-(2-Substituted Thiazol-4-yl)-2-pyridones and Thiazolo[4,5-f]quinolinones

Hiroshi Fukatsu,* Yoshiaki Kato, Satoshi Murase, and Susumu Nakagawa

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


A variety of 5-(2-substituted thiazol-4-yl)-2-pyridones and thiazolo[4,5-f]quinoliiones were synthesized and tested in vitro for cardiotonic activity. Several compounds of these series showed good positive inotropic activity.

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Paper | Regular issue | Vol 29, No. 8, 1989, pp. 1529 - 1536
Published online:
DOI: 10.3987/COM-89-4990
Synthesis of Sulfonamide Analogs of the Pyrrolo[1,4]benzodiazepine Antibiotic Abbeymycin

Nicole Langlois and Ratremaniaina Z. Andriamialisoa

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


Sulfonamide analogs of antitumor antibiotics of the pyrrolo[1,4]benzodiazepine group were prepared from (S)-prolinol as carbinolamine ethers.

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Paper | Regular issue | Vol 29, No. 8, 1989, pp. 1537 - 1543
Published online:
DOI: 10.3987/COM-89-4994
Reactions of Diazo Compounds of Heterocyclic Aldehydes with Phenylacetylene: Formation of Pyrazoles Combined with Heterocycles

Katsuhiro Saito,* Hiroshi Fushihara, Tatsuji Sato, Hiraku Ishihara, and Kensuke Takahashi

*Faculty of Engineering, Nagoya Institute of Technology, Gokiso-cho, Showa-ku, Nagoya 466-8555, Japan


Reactions of sodium salts of 2- and 3-thiophenecarbaldehyde tosylhydrazone and furfural tosylhydrazone with phenylacetylene afforded pyrazoles combined with thiophene and furan moieties via 1,3-dipolar cycloadditions of the corresponding diazo compounds.

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Paper | Regular issue | Vol 29, No. 8, 1989, pp. 1545 - 1550
Published online:
DOI: 10.3987/COM-89-5001
Reactions of Pyrazole and Pyrrole Derivatives with Trimethylchlorosilane

Katsuhiro Saito,* Yoichi Horie, Toyonobu Murase, and Kensuke Takahashi

*Faculty of Engineering, Nagoya Institute of Technology, Gokiso-cho, Showa-ku, Nagoya 466-8555, Japan


Reactions of 1-carbomethoxypyrazole and 1-carbomethoxypyrrole with trimethylchlorosilane in hexamethylphosphortriamide in the presence of magnesium afforded the parent compounds, respectively, eliminating the substituents. The similar reaction using 1-methylpyrazole gave 1-methyl-5-trimethylsilylpyrazole through a substitution reaction. The reactions are considered to proceed via radical anions of the heterocycles formed by electron transfers from magnesium.

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Paper | Regular issue | Vol 29, No. 8, 1989, pp. 1551 - 1558
Published online:
DOI: 10.3987/COM-89-5003
Imidazole Derivatives. Part II. Synthesis of Imidazo[1,2-a]pyridin-5-ones

Hans-Joachim Knölker,* Roland Boese, and Rainer Hitzemann

*Institut für Organische Chemie, Universität Hannover, Schneiderberg 1b, D-30167 Hannover, Germany


The reaction of 2-phenacylimidazole with acetylenic esters provides imidazo[1,2-a]pyridin-5-ones by an one-pot procedure.

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Paper | Regular issue | Vol 29, No. 8, 1989, pp. 1559 - 1571
Published online:
DOI: 10.3987/COM-89-5004
Reactions of Ethyl 2-Hydroxy-4-(4-hydroxy-6-methyl-2-pyron-3-yl)-4-oxo-2-butenoate with N-Nucleophiles. Synthesis of Isomeric Pyronylpyrazoles and Pyrano[4,3-c]pyrazoles

Ana Brbot-Saranovic,* Branka Katusin-Razem, and Ivana Susnik

*Institute "Ruder Boskovic", University of Zagreb, 411000 Zagreb, Croatia


Reaction of the title compound 1 with aniline gave two Schiff’s bases 2 and 3, while condensation of 1 with phenylhydrazine afforded four products 4 - 7. Compounds 4 and 6 were formed after initial nucleophilic attack at the central carbonyl carbon of tricarbonylic moiety, while 5 and 7 were formed after initial attack at the 4-position of the 2-pyrone ring. These structures were confirmed by the selective preparation of 4 - 7 from pyranopyrandiones 12 and 13, respectively. Pyrazole-4-carboxylic acid derivatives 6 and 7 cyclize in acetic anhydride into fused pyrano[4,3-c]pyrazoles 8 and 9, respectively. Their structures were compared with that of the parent 3-methyl congeners 14 and 15, obtained from dehydraacetic acid.

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Paper | Regular issue | Vol 29, No. 8, 1989, pp. 1573 - 1576
Published online:
DOI: 10.3987/COM-89-5005
Phase-transfer Catalysed Alkylation of 3-Hydroxycoumarin

Krishna C. Majumdar,* Abu T. Khan, and Shital K. Chattopadhyay

*Department of Chemistry, University of Kalyani, Kalyani 741 235, West Bengal, India


Phase-transfer catalysed alkylarion of 3-hydroxycoumarin with active alkyl halides gave O-alkylated products (45-60%), C-alkylated products (20-40%) and in one case C,O-dialkylated product (20%).

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Paper | Regular issue | Vol 29, No. 8, 1989, pp. 1577 - 1582
Published online:
DOI: 10.3987/COM-89-5006
The Structure of Two New Diterpenoid Alkaloids from Aconitum napellus L. S. Str.

Gabriel de la Fuente,* Matías Reina, and Emir Valencia

*Instituto de QUímica Orgánica, Instituto de Productos Naturales Orgánicos, C. S. I. C./ Unversidad de La Laguna, La Laguna, Tenerife, Canary Islands, Spain


From aerial parts of Aconitum napellus L. s. str. (syn. A. anglicum Stapf) were isolated two new diterpenoid alkaloids, 8-O-ethylbenzoylaconine (1) and 15-acetyl-13-dehydracardiopetamine (3), besides cardiopetamine (5), 15-acetylcardiopetamine (4), songoramine (6), and songorine (7). The structures were established by 1H - and 13C-nmr and confirmed by partial synthesis.

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Paper | Regular issue | Vol 29, No. 8, 1989, pp. 1583 - 1588
Published online:
DOI: 10.3987/COM-89-5016
Ring Transformation of 5-Acylpyrimidines into 4-Acylpyrazoles with Phenylhydrazine

Abdelilah Bajnati, Michel Hubert-Habart,* Kaname Takagi, and Hiroshi Terada

*Section de Physique et Chimie, Institut Curie, 11 rue Pierre et Marie Curie, 75231 Paris Cedex 05, France


Phenylhydrazine in alcoholic acidic medium exclusively transformed 5-benzoyl-4-methyl-2-methylthiopyrimidine into 4-acetyl-1,3-diphenylpyrazole and 5-acetyl-2-methylthio-4-phenylpyrimidine into 4-benzoyl-3-methyl-1-phenylpyrazole. The mechanism of these ring contraction reactions is proposed.

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Paper | Regular issue | Vol 29, No. 8, 1989, pp. 1589 - 1593
Published online:
DOI: 10.3987/COM-89-5017
Synthesis of Vinca Alkaloids and Related Compounds, XLV. A New Heterocyclic Ring System

Zsuzsanna Kardos-Balogh, Ferenc Sóti, Mária Incze, Mária Kajtár-Peredy, and Csaba Szántay*

*Institute of Chemistry, Chemical Research Center, Hungarian Academy of Sciences, H-1025 Budpest II, Pusztaszeri ut 59-67, P.O. Box 17, Hungary


The indole derivative 1 rearranges under acidic conditions to a new heterocyclic ring system (2). On reacting the Latter with LAH a second rearrangement takes place, and compound 3 is formed.

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Paper | Regular issue | Vol 29, No. 8, 1989, pp. 1595 - 1600
Published online:
DOI: 10.3987/COM-89-5023
New Synthetic Approach to Pyrazolo[3,4-d]pyridazin-7(6H)-one Ring System

Vittorio Dal Piaz,* Giovanna Ciciani, Maria Paola Giovannoni, and Giovanni Turco

*Dipartimento di Scienze Farmaceutiche, Università di Ferrara, via Fossato di Mortara 17, I-44100, Ferrara, Italy


Treatment of 2,6-disubstituted 5-acetyl-4-nitropyridazin-3(2H)-ones (2a-b) with hydrazine or substituted hydrazines in alcoholic medium gives rise in high yields to new 1H- and 2H-pyrazolo[3,4-d]pyridazin-7(6H)-ones (1a-f).

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Paper | Regular issue | Vol 29, No. 8, 1989, pp. 1601 - 1605
Published online:
DOI: 10.3987/COM-89-5025
Convenient Preparations of 1,8-Dioxo-6-thioxopimerazino[1,2-c]perhydropyrimidines

Tadashi Ohkawara, Shigenori Matsumoto, Tetsuo Yamasaki,and Mitsuru Furukawa

*Faculty of Pharmaceutical Sciences, Kumamoto University, 5-1 Oe-hon-machi, Kumamoto 862-0973, Japan


Hydrolysis of 4-thiocarbamoyl-3-ethoxycarbonylmethylpiperazin-2-ones 3 in alkaline solution followed by acidification afforded 1,8-dioxo-6-thioxopiperazino[1,2-c]perhydropyrimidines 4 in 65-85% yields.

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Paper | Regular issue | Vol 29, No. 8, 1989, pp. 1607 - 1613
Published online:
DOI: 10.3987/COM-89-5056
Preparation of [1,2,4]Triazolo[5,1-c][1,2,4]triazine Derivatives from 3,4-Diamino[1,2,4]triazine

Pedro Molina,* Mateo Alajarín, Ma Jesús Pérez de Vega, and Antonio López

*Departmento de Química Orgánica, Facultad de Ciencias, Universidad de Murcia, 30071 Murcia, Spain


3,4-Diamino[1,2,4]triazine 1 reacts with diarylcarbodiimides to give the 7-arylamino-3-methyl-8H-4-oxo[1,2,4]triazolo[5,1-c][1,2,4]triazines in good yields. The reaction of the iminaphosphorane 4 with thioureas leads directly to 2 in moderate yields.

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Review | Regular issue | Vol 29, No. 8, 1989, pp. 1615 - 1648
Published online:
DOI: 10.3987/REV-89-393
Pyrazole 1-Oxides, 1,2-Dioxides and Derivatives

Antigoni Kotali and Petros G. Tsoungas

*Laboratory of Organic Chemistry, College of Engineering, University of Thessaloniki, Thessaloniki 54006, Greece


Structure, syntheses, spectroscopic properties and the chemical reactivity of the N-oxides of the pyrazole nucleus are described.

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26 data found. 1 - 26 listed