Regular Issue

Vol. 23, No. 6, 1985

29 data found. 1 - 29 listed
Communication | Regular issue | Vol 23, No. 6, 1985, pp. 1353 - 1356
Published online:
DOI: 10.3987/R-1985-06-1353
Amidoalkylation of Aromatic Compounds with Methylglyoxal-bismethylcarbamate. A New Synthesis of 1-Amino-1-phenyl-2-propanone Derivatives and Substituted Benzofurans

Dov Ben-Ishai* and Daniella Denenmark

*Department of Chemistry, Israel Institute of Technology, Haifa 32000, Israel

Abstract

The synthesis of 1-methoxycarbonylamino-1-aryl-2-propanones 4 and 3-methoxy carbonylamino-3-methylbenzofurans 7 by the direct amidoalkylation of aromatic compounds with methylglyoxal-bismethylcarbamate (3) is described. The amidopropanones (4) were further converted to the corresponding amidopropanols (5) and 2-oxazolidinones (6).

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Communication | Regular issue | Vol 23, No. 6, 1985, pp. 1357 - 1361
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DOI: 10.3987/R-1985-06-1357
Two New Morphinane Alkaloids from Beilschmiedia oreophila Schlechter (Lauraceae)

François Tillequin, Michel Koch,* Jacques Pusset, and Gérard Chauvière

*U.A. au C.N.R.S.n°484, Faculté des Sciences Pharmaceutiques et Biologiques, Université René Descartes, 4, Avenue de l‘Observatoire, F-75006 Paris, France

Abstract

Two new morphinane alkaloids, oreobeiline (1) and 6-epioreobeiline (2) have been isolated from the stem bark and wood of Beilschmiedia oreophila Schlechter. Their structures have been elucidated by spectroscopic studies and chcmical correlations.

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Communication | Regular issue | Vol 23, No. 6, 1985, pp. 1363 - 1366
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DOI: 10.3987/R-1985-06-1363
N,N’-Dialkyl-pyrazinium and Quinoxalinium Salts. N-Heterocycloc Redox Systems with the Radical Cation Intermediate as Most Persistent Oxidation State

Wolfgang Kaim*

*Institut für Anorganische, Niederurseler Hang, D-6000 Frankfurt am Main 50, Germany

Abstract

Two-step redox systems with the cation radical intermediate as most persistent oxidation state were found in electrochemical and ESR studies of the title compounds. The potentials measured in H2O and DMF range from -0.7 V to +0.7 V vs. saturated calomel electrode.

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Communication | Regular issue | Vol 23, No. 6, 1985, pp. 1367 - 1371
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DOI: 10.3987/R-1985-06-1367
Conformational Studies of 1- and 3-Ethyl-1,2,3,4,6,7,12,12b-octahydroindolo[2,3-a]quinolizines

Mauri Lounasmaa,* Reija Jokela, and Tarja Tamminen

*Laboratory of Organic Chemistry, Helsinki University of Technology, P.O. Box 6100,FIN-02015 HUT, Espoo, Finland

Abstract

A mainly 13C NMR based conformational study of the 1- and 3-ethyl-1,2,3,4,6,7,12,12b-octahydroindolo[2,3-a]quinolizines 1-4 is presented.

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Communication | Regular issue | Vol 23, No. 6, 1985, pp. 1373 - 1376
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DOI: 10.3987/R-1985-06-1373
Intermolecular Photoaddition of N-Methylphthalomide to Indole Derivatives: Regio- and Stereoselective Formation of Oxeto[2,3-b]indoles

Haruko Takechi,* Minoru Machida, and Yuichi Kanaoka

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

Abstract

N-Methylphthalimide in the presence of N-acylindole derivatives underwent a photochemical [2+2]cycloaddition to give more sterically hindered oxetanes in moderate yields. Some reactions of these imide-oxetanes are also described.

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Communication | Regular issue | Vol 23, No. 6, 1985, pp. 1377 - 1380
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DOI: 10.3987/R-1985-06-1377
A Total Synthesis of (±)-Lysergol, a 9-Ergolene Type of Ergot Alkaloi

Toshiko Kiguchi, Chiyomi Hashimoto, and Ichiya Ninomiya*

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

Abstract

According to the synthetic route established on the despyrrole analog of the alkaloid, the first total synthesis of (±)-lysergol was completed.

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Communication | Regular issue | Vol 23, No. 6, 1985, pp. 1381 - 1384
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DOI: 10.3987/R-1985-06-1381
Formation of Novel Heterocycles, [1]Benzothiopyrano[3,4-b]pyrrole Derivatives by Unusual Cyclixation Reaction of 1-Benzothiopyran-1-oxide Derivatives

Mikio Hori,* Tadashi Kataoka, Hiroshi Shimizu, Eiji Imai, Noriyuki Iwata, Norihiko Kawamura, and Masayasu Kurono

*Department of Pharmacognosy, Gifu College of Pharmacy, 6-1 Mitahora-higashi 5-chome, Gifu 502-8585, Japan

Abstract

Treatment of 1-benzothiopyran-1-oxide derivatives (12a,b) with sulfuryl chloride and then with sodium hydride afforded a novel type of derivatives of [1]benzothiopyrano[3,4-b]pyrrole.

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Communication | Regular issue | Vol 23, No. 6, 1985, pp. 1385 - 1390
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DOI: 10.3987/R-1985-06-1385
A Short Synthesis of Rutecarpine and/or Vasicolinone from 2-Chloro-3-(indol-3-yl)ethylquinazolin-4(3H)-one: Evidence for the Participation of the Spiro Intermediate

Chikara Kaneko,* Takuo Chiba, Kouichi Kasai, and Chiemi Miwa

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

Abstract

A new route to rutecarpine and/or vasicolinone from 2-chloro-4-quinazolone through an acid catalyzed cyclization of 2-chloro-3-indolylethylquinazolin-4-one has been developed and the mechanism of the cyclization reaction clarified.

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Communication | Regular issue | Vol 23, No. 6, 1985, pp. 1391 - 1393
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DOI: 10.3987/R-1985-06-1391
Dihydroxygirinimbine, a New Carbazole Alkaloid from Murraya euchrestifolia

Hiroshi Furukawa,* Tian-Shung Wu, and Chang-Sheng Kuoh

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

Abstract

Dihydroxygirinimbine (1) was the first isolated from the root bark of Murraya euchrestifolia Hayata, and the structure was established by spectroscopic analysis and the transformation of girinimbine (3).

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Communication | Regular issue | Vol 23, No. 6, 1985, pp. 1395 - 1398
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DOI: 10.3987/R-1985-06-1395
1,3-Dipolar Cycloaddition Reaction of Chromones and Coumarin with Pyridinium Ylides

Ichiro Yokoe,* Shunsuke Matsumoto, Yoshiaki Shirataki, and Manki Komatsu

*Faculty of Pharmaceutical Sciences, Josai University, 1-1 Keyakidai, Sakado, Saitama 350-0295, Japan

Abstract

1,3-Dipolar cycloaddition reaction of N-iminopyridinium ylide (2) with chromones (1) gave pyrazolo[1,5-a]pyridines (3) in moderate yields. Similarly coumarin (4) reacted with 2 to give 6H-[1]-benzopyrano [4’,3’:3,4]pyrazoro[1,5-a]pyridin-6-one (5) . Furthermore chromone (1) was cyclized with pyridinium phenacylide (6) to afford 1-(2’-hydroxybenzoyl)-3-benzoylindolizine (7)

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Communication | Regular issue | Vol 23, No. 6, 1985, pp. 1399 - 1402
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DOI: 10.3987/R-1985-06-1399
Boron Trifluoride Etherate-catalysed Rearrangement of 2,4,6,7-Tetraphenyl-1,3-oxazepine to Give Novel Pyridone Ring System

Tomoshige Kobayashi and Makoto Nitta*

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

Abstract

The boron trifluoride etherate causes an efficient rearrangement of 2,4,6,7-tetraphenyl-1,3-oxazepine to lead to 2,2,4,6-tetraphenyl-3-pyridone and 3,3,4,6-tetraphenyl-2-pyridone. The BF3-coordinated pyridine-2,3-oxide is proposed as a reasonable intermediate.

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Report | Regular issue | Vol 23, No. 6, 1985, pp. 1403 - 1409
Published online:
DOI: 10.3987/R-1985-06-1403
The Trapping of Sulfenic Acids from Penicillin Sulfoxides. Aryl Mercaptans

Ronald G. Micetich,* Samarendra N. Maiti, Motoaki Tanaka, Tomio Yamazaki, and Kazuo Ogawa

*Faculty of Pharmacy and Pharmaceutical Sciences, University of Alberta, Edmonton, Alberta, T6G 2G2, Canada

Abstract

Aryl mercaptans, unlike heterocyclic mercaptans, reacted exceptionally slowly with penicillin sulfoxides. These reactions are affected by the substituent at the C-6 position of the penam, and by the nature of the ester group at the C-3 position. The unsym-azetidinone disulfides obtained from these reactions, unlike those from heterocyclic mercaptans, did not react with halogenating agents such as cupric chloride.

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Report | Regular issue | Vol 23, No. 6, 1985, pp. 1411 - 1415
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DOI: 10.3987/R-1985-06-1411
Homolytical Alkylation of Heteroaromatic Bases by Cyclic Acetals

Semen Solomonovitch Zlotsky,* Vladimir Victorovitch Sorin, Yuri Borisovitch Seletchonok, and Dilus Lutfullitch Rakhmankulov

*Ufa Oil Institute, Kosmonavtov Str., 1, Ufa, 450062, Russia

Abstract

Homolytical reaction between protonated bases and 1,3-diheterocycloalkanes was described.

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Report | Regular issue | Vol 23, No. 6, 1985, pp. 1417 - 1423
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DOI: 10.3987/R-1985-06-1417
Heterocyclic Systems. V. Synthesis of 1H,4H,6H-Pyrazolo[3,4-e]pyrrolo[2,1-c][1,4]oxazepine Derivatives

Silvio Massa, Giorgio Stefancich, Marino Artico,* Federico Corelli, and Giovannni Ortenzi

*Isitituto de Chimica farmaceutica e tossicologica, Facolta di Farmacia, Università a degli Studi di Roma "La Sapienza", Piazza Aldo Moro, 5 - 00185 Roma, Italy

Abstract

The synthesis of derivatives of a new tricyclic heteroaromatic ring, 1H,4H,6H-pyrazolo[3,4-e]pyrrolo[2,1-c][1,4]oxazepine, is described. Formylation of 4-ethoxycarbonyl-1-phenyl-5-(1-pyrryl)pyrazole, prepared from 5-amino-4-ethoxycarbonyl-1-phenylpyrazole by Clauson-Kaas method, afforded 4-ethoxycarbonyl-5-(2-formyl-1-pyrryl)-1-phenylpyrazole, which was then reduced to 4-hydroxymethyl-5-(2-hydroxymethyl-1-pyrryl)-1-phenylpyrazole. Treatment of the diol with phosphorus pentoxide led to 1-phenyl-1H,4H,6H-pyrazolo[3,4-e]pyrrolo[2,1-c][1,4]oxazepine. 4-Methyl and 4-phenyl derivatives of the latter compound were also prepared.

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Report | Regular issue | Vol 23, No. 6, 1985, pp. 1425 - 1430
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DOI: 10.3987/R-1985-06-1425
TiCl4-Induced Functionalisation of Dibenzo[b,f][1,4]diazocine-6,11-(5H,12H)-diones

Bindumadhavan Venugopalan,* Sivasailam Suresh Iyer, and Noel John de Souza

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

Abstract

Dibenzo[b,f][1,4]diazocine-6,11-diones (1) were converted to the corresponding 6,11-disubstituted amino derivatives (3) when treated with secondary amines in the presence of titanium tetrachlorideanisole complex. Formation of the (benzimidazol-2-yl)benzamides (4) as the side products was observed in the case of substituted 1.

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Report | Regular issue | Vol 23, No. 6, 1985, pp. 1431 - 1435
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DOI: 10.3987/R-1985-06-1431
The Behaviour of Vicinal Alkyl Aminothiophenecarboxylates in the Sandmeyer and Schiemann Reactions

Carlos Corral,* Ana Lasso, Jaime Lissaveyzky, Alberto Sánchz Alvarez-Insúa, and Ana M. Valdeolmillos

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

Abstract

The diazotization of vicinal alkyl aminothiophenecarboxylates has been studied. 3-Amino compounds gave clear diazonium salts which yielded the expected halo derivatives in the Sandmeyer and Schiemann conditions. However, 2-amino compounds yielded self-coupling products.

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Report | Regular issue | Vol 23, No. 6, 1985, pp. 1437 - 1444
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DOI: 10.3987/R-1985-06-1437
Phosphorus Pentoxide in Organic Synthesis - Part 23. Synthesis of 1,2,3,4-tetrahydro-9-acridinamines

Peter Finlander, Hans Peter Fischer, and Erik Bjerregaard Pedersen*

*Department of Chemistry, Odense University, Campusvej 55 DK-5230 Odense M., Denmark

Abstract

1,2,3,4-Tetrahydro-9(10H)-acridinone 2 was synthesized from methyl anthranilate and cyclohexanone using a mixture of P2O5 and N,N-dimethylcyclohexylamine as a condensing reagent. 1,2,3,4-Tetrahydro-9-acridinamines 3 were prepared, either directly from 2, using the new phosphoric amide reagents, or via the corresponding 9-chloro derivative 7 by reaction with amines.

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Report | Regular issue | Vol 23, No. 6, 1985, pp. 1445 - 1450
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DOI: 10.3987/R-1985-06-1445
Oxodation Studies of Beta-lactam Antibiotics. The 6(7)-Iminoethers of Penicillins and Cephalosporins

Ronald G. Micetich* and Rajeshwar Singh

*Faculty of Pharmacy and Pharmaceutical Sciences, University of Alberta, Edmonton, Alberta, T6G 2G2, Canada

Abstract

The oxidation of the 6-iminoethers of penicillins using m-CPBA gave the 1β-sulfoxide of the respective 6-iminoerher; whereas with H2O2-CH3CO2H, the 6-iminoetherpenicillins and 7-iminoethercephalosparins gave the respective 1β-sulfoxides of the 6(7)-amido compounds

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Report | Regular issue | Vol 23, No. 6, 1985, pp. 1451 - 1457
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DOI: 10.3987/R-1985-06-1451
Synthesis of the Alkaloids and Laurifonine Using a Chloroformate-madiated Ring Expansion

John B. Bremner* and Charles Dragar

*Department of Chemistry, University of Tasmania, GPO Box 252C Hobart, Tasmania, 7001, Australia

Abstract

A convenient synthesis of the reduced dibenz[d,f]azonine ring system is described affording laurifonine in 29% overall yield from homoveratrylamine. The alkaloid laurifine is also accessible in 15% overall yield (as the oxalate salt) by the same route, which employs a methyl chloroformate-induced ring expansion of an erythrinan-3-one derivative.

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Report | Regular issue | Vol 23, No. 6, 1985, pp. 1459 - 1464
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DOI: 10.3987/R-1985-06-1459
Termolysis of 4-Azidopyrimidines and 4-Azidoquinazolines

Lorenzo Giammanco* and Francesco Paolo Invidiata

*Instituto di Chimica Farmaceutica e Tossicologica, Università digli Studi di Palermo, Via Archirafi 32, 90123 Palermo, Italy

Abstract

A facile thermolysis of 4-azidopyrimidines and 4-azidoquinazolines leading, by ring contraction, in excellent yields to 1-cyanoimidazoles and benzimidazoles is reported.

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Report | Regular issue | Vol 23, No. 6, 1985, pp. 1465 - 1469
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DOI: 10.3987/R-1985-06-1465
New Difunctionalaized 4-Nitroisoxazoles from α-Nitroacetophenone Oxime

Rodolfo Nesi,* Stefano Chimichi, Piero Sarti-Fantoni, Annalisa Buzzi, and Donatella Giomi

*CNR, Centro di Studio Sulla Chimica e la Struttura dei Composti Eterociclici e lolo Applicazioni, c/o Dipartimento di Chimica Organica "Ugo Schiff", Università di Firenze, Via Gino Capponi 9, I-50121 Firenze, Italy

Abstract

The title compound (1) reacted smoothly with the acyl chlorides (2a-d) to give the derivatives (3a-d) which were converted in high yields into the nitroisoxazoles (4a-d), respectively, through a base-induced cyclization.

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Report | Regular issue | Vol 23, No. 6, 1985, pp. 1471 - 1477
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DOI: 10.3987/R-1985-06-1471
Thienopyrrolizidines II. Synthesis of 4-Imino (and 4-amino)-4H-thieno[2,3-b]pyrrolizines

Catherine Laporte-Wojcik, Anne-Marie Godard, Sylvain Rault, and Max Robba*

*Laboratoire de Chimie Thérapeutique, U. F. R. des Sciences Pharmaceutiques, Université de Caen, 1, rue Vaubénard, 14032 Caen Cedex, France

Abstract

Vilsmeier’s thienopyrroliziniminium salts were treated with primary amines to give N-substitued thienopyrrolizinimines. Reduction of these imines gave the corresponding amino derivatives.

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Report | Regular issue | Vol 23, No. 6, 1985, pp. 1479 - 1482
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DOI: 10.3987/R-1985-06-1479
A Novel Synthesis of 1,6-Dihydro-2-methyl-6-oxo[3,4’-bipyridine]-5-carbonitrile (Milrinone)

Baldev Singh*

*Sterling Research Group, Rensselaer, New York 12144, U.S.A.

Abstract

Milrinone (3) was prepared either by reacting ethoxymethylenemalononitrile with 1-(4-pyridinyl)-2-propanone or malononitrile with 4-ethoxy-3-(4-pyridinyl)-3-buten-2-one.

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Report | Regular issue | Vol 23, No. 6, 1985, pp. 1483 - 1491
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DOI: 10.3987/R-1985-06-1483
Synthesis of Phenolic Metanolites of an Antifugal Imidazole Derivatives (Cloconazole Hydrochloride)

Kimio Takahashi, Sumio Shimizu, and Masaru Ogata*

*Shionogi Research Laboratories, Shionogi & Co. Ltd., Fukushima-ku, Osaka 553-0002, Japan

Abstract

Syntheses of phenolic metabolites of antifungal vinylimidazole derivative 6·HCl (Cloconazole hydrochloride) are described. Phenolic compound 8 was prepared from 2 using selective mono THP protection, followed by imidazolation and deprotection. 10 was synthesized from 12 and spontaneously decomposed to 4 and 19 in acidic methanol. Synthesis of 11 started from 20 via nucleophilic aromatic substitution to introduce an oxygen function at the m-position of the chlorine substituent.

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Report | Regular issue | Vol 23, No. 6, 1985, pp. 1493 - 1496
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DOI: 10.3987/R-1985-06-1493
Organogermanium Compounds. New Simplified Synthesis of Germatranes Substituted with Novel Functional Groups

Norihiro Kakimoto,* Katsuyuki Sato, Toyozo Takada, and Mitsuo Akiba

*Asai Germanium Research Institute, 1-6-4, Izumihon-cho, Komae-shi Tokyo 201, Japan

Abstract

New general methods for the synthesis of 5-substituted germatranes (4) have been directly developed using the corresponding germyl adducts (2) obtained by germylation of α,β-unsaturated compounds (1) with trichlorogermane.

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Report | Regular issue | Vol 23, No. 6, 1985, pp. 1497 - 1501
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DOI: 10.3987/R-1985-06-1497
Synthesis of (5-Styryl-2-thienyl)-phenylacrylic Acids

Grace Karminski-Zamola* and Miro Bajic

*Organic Chemistry Department, Faculty of Technology, University of Zagreb, Marulicev trg 20, 41000 Zagreb, Croatia

Abstract

We describe the synthesis of E-3-(5-styryl-2-thienyl)-2-phenylacrylic acid 7, E-3-(5-styryl-2-thienyl)-2-(4-methoxyphenyl)acrylic acid 8, E-3-[5-(4-methoxyphenylethenyl)-2-thienyl]-2-phenylacrylic acid 9 and E-3-[5-(4-methoxyphenylethenyl)-2-thienyl]-2-(4-methoxyphenyl)acrylic acid 10 by Oglialoro condesation.

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Report | Regular issue | Vol 23, No. 6, 1985, pp. 1503 - 1508
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DOI: 10.3987/R-1985-06-1503
A 400 MHz 1H NMR Study of Twelve Ajmaline-type Alkaloids

Mauri Lounasmaa* and Reija Jokela

*Laboratory of Organic Chemistry, Helsinki University of Technology, P.O. Box 6100,FIN-02015 HUT, Espoo, Finland

Abstract

The chemical shifts and most of the main coupling constants of twelve ajmaline alkaloids 1 - 12 determined in a 400MHz 1H NMR study.

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Report | Regular issue | Vol 23, No. 6, 1985, pp. 1509 - 1512
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DOI: 10.3987/R-1985-06-1509
Mono- and Di-substituted 3-Aza-α-tropolones

Yoshie Horiguchi, Takehiro Sano,* and Yoshisuke Tsuda

*Showa Pharmaceutical University, 3-3165, Higashi-tamagawagakuen, Machida, Tokyo 194-8543, Japan

Abstract

New mono- and di-substituted 3-aza-α-tropolones 6 were synthesized by deethoxycarbonylation and subsequent DDQ oxidation of dihydroazatropolones 4. In methanol, 6 undergoes a skeletal rearrangement to give methyl pyridine-2-carboxylates 7, suggesting that the reaction is characteristic of the azatropolone nucleus.

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Review | Regular issue | Vol 23, No. 6, 1985, pp. 1513 - 1554
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DOI: 10.3987/R-1985-06-1513
The Chemistry of N-Substituted Pyridinium Salts

Wanda Sliwa,* Grazyna Matusiak, and Anna Postawka

*Institute of Chemistry, Pedagogical University, 25-020 Kielce, Poland

Abstract

Syntheses, physicochemical and biological properties of N-substituted pyridinium salts, as well as their applications are described.

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29 data found. 1 - 29 listed