Regular Issue

Vol. 31, No. 8, 1990

27 data found. 1 - 27 listed
Communication | Regular issue | Vol 31, No. 8, 1990, pp. 1393 - 1936
Published online:
DOI: 10.3987/COM-89-5238
Triazinobenzothiazine — A New Heterocyclic System via a Novel Cyclization Reaction

John H. Musser,* Susan C. Lewis, and Reinhold H. W. Bender

*Wyeth-Ayerst Research Inc., CN 8000, Princeton, NJ 08543-8000, U.S.A.


The synthesis and X-ray structure of 9-chloro-2,4-dimethyl[1,3,5]triazino[2,1-c]-1,4-benzothiazine-1,3(2H,4H)-dione (2) are reported. A mechanism is proposed for the formation of this novel heterocyclic system.

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Communication | Regular issue | Vol 31, No. 8, 1990, pp. 1397 - 1403
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DOI: 10.3987/COM-89-5259
Regioselective Synthesis of Optically Active (R)-5-Methyl- and (R)-7-Methyl-5,6,7,8-tetrahydroquinolines

Giorgio Chelucci,* Sergio Cossu, Gianfranco Scano, and Francesco Soccolini

*Department of Chemistry, University of Sassari, Via Vienna 2, I-07100 Sassari, Italy


Five synthetic routes have been evaluated for the regioselective preparation of (R)-5-methyl- and (R)-7-methyl-5,6,7,8-tetrahydroquinolines from (+)-(R)-3-methylcyclohexanone.

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Communication | Regular issue | Vol 31, No. 8, 1990, pp. 1405 - 1408
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DOI: 10.3987/COM-90-5394
Furanoeremophilanes from Senecio andreuxii

Benito Reyes and Guillermo Delgado*

*Instituto de Química, Universidad Nacional Autónama de México, Ciudad Universitaria, Circuito Exterior, Coyoacán 04510, Mexico


From the leaves of Senecio andreuxii (Compositae) two new furanoermophilanes, 1-deacetyl-6-angeloyl-2,3-deoxy-hilliardinol (1) and 3α-angeloxy-6β-senecioyloxy-10βH-furanoeremophil-9-one (2), and the known 3, were isolated and structurally elucidated.

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Communication | Regular issue | Vol 31, No. 8, 1990, pp. 1409 - 1412
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DOI: 10.3987/COM-90-5425
Phenolic Compounds from Salix sachalinensis

Mizuo Mizuno,* Masaya Kato, Nobue Hosoi, Munekazu Iinuma, Toshiyuki Tanaka, Akira Kimura, Hiroyoshi Ohashi, Hideki Sakai, and Tadashi Kajita

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


Two new glucosides of phenolic compounds, sachalisides 1 (1) and 2 (2), were isolated from the bark of Salix sachalinensis and their structures were established by the spectroscopic analysis. The aglycone moiety of sachalisdie 2 was a new type skeleton consisting of C6-C3-C6-C3-C6 units (flavan-3-ol substituted with phenylpropanoid on the A-ring).

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Communication | Regular issue | Vol 31, No. 8, 1990, pp. 1413 - 1416
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DOI: 10.3987/COM-90-5427
Preparation of Newly Modified DIOP Bearing Bis(4-dimethylamino-3,5-dimethylphenyl)phosphino Groups and Its Application to Efficient Asymmetric Hydrogenation of Itaconic Acid Derivatives

Kiyoshi Yoshikawa, Kiyoshi Inoguchi, Toshiaki Morimoto, and Kazuio Achiwa*

*Schol of Pharmaceutical Sciences, University of Shizuoka, 395 Yada, Shizuoka 422-8526, Japan


We prepared a modified DIOP analogue bearing bis(4-dimethylamino-3,5-dimethylphenyl)phosphinogroups. Its rhodium complex was found to be a useful catalyst for asymmetric hydrogenation of dimethyl itaconate and itaconic aicd derivatives bearing β-aryl goups.

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Communication | Regular issue | Vol 31, No. 8, 1990, pp. 1417 - 1421
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DOI: 10.3987/COM-90-5432
I2-Induced Enoletherification of α-Allyl Substituted β-Keto Sulfones; A Route to 3-Phenylsulfonyl-2,5-disubstituted Furans

Jae Wook Lee and Dong Young Oh*

*Korea Advanced Institute of Science and Technology, 373-1, Kusong-Dong, Yusung-Gu, Taejon, Korea


Iodine-induced enoletherification of α-allyl substituted β-keto sulfones leads to 4,5-dihydro-5-iodomethylfurans which are readily converted to 3-phenylsulfonyl-2,5-disubstituted furans.

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Communication | Regular issue | Vol 31, No. 8, 1990, pp. 1423 - 1426
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DOI: 10.3987/COM-90-5448
Rearrangement of Exomethylenecephams to Homocephams

John M. Morin, Jr.,* Douglas O Spry, Thomas K. Elzey, Michael D. Kinnick , Jonathan W. Paschal, and Nancy J. Snyder

*Lilly Reserach Laboratories, Eli Lilly & Company, Lilly Corporate Center, Indianapolis, IN 46285-4813, U.S.A.


Exomethylenecephams rearrange by reaction with diazo compounds in the presence of cupric sulfate to generate the homocepham ring-system.

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Communication | Regular issue | Vol 31, No. 8, 1990, pp. 1427 - 1429
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DOI: 10.3987/COM-90-5454
A New Heterocycle with Analgesic Activity: 2,6-Epoxy-1,2,3,4,5,6-hexahydro-3-methyl-3-benzazocine

Bernhard Wünsch,* Georg Höfner, and Gerd Bauschke

*Institut für Pharmazie und Lebensmittelchemie der Universität München, Sophienstr. 10, 8000 München 2, Germany


The title compound (4) was prepared in five steps, starting with the benzaldehyde derivative (5). In the mouse writhing-test 4 showed strong analgesic activity.

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Communication | Regular issue | Vol 31, No. 8, 1990, pp. 1431 - 1433
Published online:
DOI: 10.3987/COM-89-5382
Tandem Michael Addition-[3,3] Sigmatropic Rearrangement Processes — A Concise Route to Functionalized 3-Alkoxycarbonylindoles

Masahiro Toyota and Keiichiro Fukumoto*

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


The synthesis of methyl indole-3-carboxylate (4) and methyl 6-methoxyindole 3-carboxylate (7) by tandem Michael addition-[3,3] sigmatropic rearrangement reaction is described.

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Communication | Regular issue | Vol 31, No. 8, 1990, pp. 1435 - 1438
Published online:
DOI: 10.3987/COM-90-5460
Imidazole Derivatives. Part V. Imidazo[1’,2’:1,6]pyrdio[2,3-d]pyridazine: Synthesis, Structure, and Preliminary Chemistry of a Novel Heterocyclic Ring System

Hans-Joachim Knökler,* Roland Boses, and Rainer Hitzemann

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


Reaction of functionalized imidazo[1,2-a]pyridines with hydrazine hydrate to the novel imidazo[1’,2’:1,6]pyrido[2,3-d]pyridazine ring system is described.

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Paper | Regular issue | Vol 31, No. 8, 1990, pp. 1439 - 1444
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DOI: 10.3987/COM-89-5082
Pentacyclic Indole Alkaliods: A Short Synthesis of (±)-N(a)-Benzyl-20-desethylaspidospermidine

Daniel Gardette, Jean-Claude Gramain,* and Marie-Eve Sinibaldi

*Chimie des Substances Naturelles, URA 485 CNRS, Université Blaise Pascal (Clermont II), 63177 Aubière Cedex, France


The synthesis of (±)-N(a)-benzyl-20-desethylaspidospermidine in 8 steps and 25% overall yield from cyclohexanedione is described.

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Paper | Regular issue | Vol 31, No. 8, 1990, pp. 1445 - 1450
Published online:
DOI: 10.3987/COM-90-5321
The [3+2] Intramolecular Cycloaddition Reaction of Azomethine Ylides Generated from Benzylic N-Oxides

Georges Roussi

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


Benzylic azomethine ylides (Y) generated by deprotonation of the corresponding tertiary amine N-oxides (1a, 1b, 4) react intramolecularly with the suitably positioned unactivated double bond to yield the corresponding fused membered pyrrolidines (2a, 2b, 5). A competitive evolution of the ylide is observed at low temperature leading to the corresponding head to head piperazines (3, 6, 8).

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Paper | Regular issue | Vol 31, No. 8, 1990, pp. 1451 - 1458
Published online:
DOI: 10.3987/COM-90-5326
N-[2(1H)-Perimidinylmethyl]azinium Salts. Their Synthesis and Reaction with Electrophiles

Andrés Molina, Ana M. Cuadro, Julio Alvarez-Builla,* Juan J. Vaquero, and José L. Garcia Navio

*Departamento de Química Orgánica, Universidad de Alcalá de Henares, 28871 Alcalá de Henares (Madrid), Spain


A synthesis of new 2-substituted 1H-perimidines by the reaction of 1-[(methylthio)thiocarbonylmethyl]azinium salts and 1,8-diaminonaphthalene is described. Reaction of these perimidine derivatives with several electrophiles is also reported.

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Paper | Regular issue | Vol 31, No. 8, 1990, pp. 1459 - 1471
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DOI: 10.3987/COM-90-5386
The Reaction of 8-Methylpyrrolo[1,2-a]pyrazines with Dimethyl Acetylenedicarboxylate

Paul V. S. Kong Thoo Lin,* Robert Buchan, Martin Fraser, and Derek McHattie

*MRC, Labratory of Molecular Biology, Hills Road, Cambridge, CB2 2QH, U.K.


2,8-Dimethylpyrrolo[1,2-a]pyrazine reacts with two molecular proportions of dimethyl acetylenedicarboxylate (DMAD) in toluene to give a reaction mixture from which five crystalline products were isolated. Four of the products were shown to be the isomeric tetracarbomethoxy 1:2 addcuts (9, 10, 14 and 15) and the fifth to be the tricarbomethoxydipyrrolopyrazine (7). A likely common reaction intermediate leading to the formation of all five products is suggested to be the 1:1 adduc (21). Reaction of 2,3,8-trimethylpyrroo[1,2-a]pyrazine with DMAD in toluene gave the corresponding compounds (17, 18, 19, 20 and 16).

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Paper | Regular issue | Vol 31, No. 8, 1990, pp. 1473 - 1475
Published online:
DOI: 10.3987/COM-90-5397
Isonoyaine, a New C-Ring Secocularine Alkaloid

Olga Blanco, Luis Castedo,* Diego Cortes, and M. Carmen Villaverde

*Departamento de Química Orgánica, Facultad de Química, Universidad de Santiago de Compostela, E-15706, Santiago de Compostela, Spain


We report the isolation of isonoyaine (1), a new C-ring secocularine alkaloid, from Sarcocapnos saetabensis. Its structure was established on the basis of its spectroscopic data and confirmed by total synthesis

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Paper | Regular issue | Vol 31, No. 8, 1990, pp. 1477 - 1484
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DOI: 10.3987/COM-90-5406
Synthesis of Aspidosperma Alkaloids: Eight-membered vs. Six-membered Ring D Formatnion

Monique Dufour, Jean-Claude Gramain,* Henri-Philippe Husson, Marie-Eve Sinibaldi, and Yves Troin

*Chimie des Substances Naturelles, URA 485 CNRS, Université Blaise Pascal, 63177 Aubière Cedex, France


Unusual cyclization of the acetyl chain borne at C-20 of a tetracyclic intermediate (11a) or (11b) led to the formation of a pentacyclic analog of aspidosperma alkaloids with an eigth-membered ring D.

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Paper | Regular issue | Vol 31, No. 8, 1990, pp. 1485 - 1490
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DOI: 10.3987/COM-90-5423
Synthesis of Nectriafurone, an Isofuranonaphthoquinone Isolated from the Fungus Nectria haematococca

Michel Devys, Michel Barbier,* and Denise Parisot

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


Synthesis of 5-methoxy-4,7-dihydroxynaphtho[2,3-c]8,9-furandione (2) and of 4,7-dihydroxynaphtho[2,3-c]8,9-furandione (3) were carried out by a rapid Friedel-Crafts reaction using the dry method. The addition of acetaldehyde on 2 in presence fo LDA gave the (±)-nectriafurone (1), thus cofirming the proposed structure of 3-(1‘-hydroxyethyl)-5-methoxy-4,7-dihydroxynaphtho[2,3-c]8,9-furandione.

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Paper | Regular issue | Vol 31, No. 8, 1990, pp. 1491 - 1496
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DOI: 10.3987/COM-90-5428
Reaction of Azepines with Palladium (II) Acetate: Formation of Mucondialdehyde and Dihydroazepine Derivative

Katsuhiro Saito,* Masatoshi Kozaki, and Kensuke Takahashi

*Department of Applied Chemistry, Nagoya Institute of Technology, Gokiso-cho, Showa-ku, Nagoya 466, Japan


Reaction of 1-carboethoxy-1H-azepine with palladium (II) acetate in chloroform or acetonitrile afforded trans-trans-mucodialdehyde together with ethyl carbamate. On the other hand, the analogous reaction in acetic acid gave 1-carboethoxy-2,3-diacetoxy-2,3-dihydro-1H-azepine. The same reaction but using 1-carboethoxy-1H-1,2-diazepine gave a nitrile derivative via a ring opening.

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Paper | Regular issue | Vol 31, No. 8, 1990, pp. 1497 - 1504
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DOI: 10.3987/COM-90-5434
Synthesis of Some Conformationally Restricted Analogs of Serotonin

John E. Macor* and Kevin Ryan

*Department of Medical Chemistry, Central Research Division, Pfizer Inc., Groton, Connecticut 06355, U.S.A.


3-(2-Aminocycloalkyl)-5-methoxyindoles (3) have been synthesiezed via a three setp procedure starting with 5-methoxyindole. These molecules represent conformationally restricted analogs of serotonin.

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Paper | Regular issue | Vol 31, No. 8, 1990, pp. 1505 - 1511
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DOI: 10.3987/COM-90-5441
Palladium-catalyzed Reaction of 3-Bromoindole Derivative with Allyl Esters in the Presence fo Hexa-n-butyldistannane

Yuusaku Yokoyama, Masato Ikeda, Masaaki Saito, Tomoko Yoda, Hideharu Suzuki, and Yasuoki Murakami*

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


The palladium-catalyzed cross-coupling reaction of ethyl 3-bromo-1-tosylindole-2-carboxylate (9) with a variety of substituted allylic acetates or carbonates (10) in the presence of hexa-n-butyldistannane (6) gave 3-allylated indoles (11) in high yields.

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Paper | Regular issue | Vol 31, No. 8, 1990, pp. 1513 - 1516
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DOI: 10.3987/COM-90-5443
Deuterioformylation by the Oxonolysis of 2-Deuterio-5-phenyl- or 5-Deuterio-2-phenyloxazoles

Choji Kashima* and Hideki Arao

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


The oxonolysis of 5-deuterio-2-phenyloxazole (1b) gave deuterioformic benzoic anhydride (3b) and N-formylbenzamide (4). The reaction of the ozonolysate of 1b with various nucleophiles is not practical due to the formation of 4. Since 2-deuterio-5-phenyloxazole (2b) gave 3b quantitatively under the same conditions, the ozonolysis of 2b is concluded to be a more practical and convenient preparation of the deuterioformylating agents.

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Paper | Regular issue | Vol 31, No. 8, 1990, pp. 1517 - 1524
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DOI: 10.3987/COM-90-5447
Studies on the Alkaloids from Aconitum contortum (I)

Kazuaki Niitsu,* Yukinobu Ikeya, Hiroshi Mitsuhashi, Chen Siying, and Liang Huiling

*Research Institute for Biology & Chemistry, Tsumura & Co., 3586 Yoshiwara, Ami-machi, Inashiki-gun, Ibaraki, 300-11, Japan


A new diterpenoid alkaloid, contortumine (1), and seven known diterpenoid alkaloids were isolated from the roots of Aconitum contortum. Structures of these alkaloids were determined on the basis of spectral and chemical data.

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Paper | Regular issue | Vol 31, No. 8, 1990, pp. 1525 - 1535
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DOI: 10.3987/COM-90-5452
Asymmetric Synthesis of (+)- and (-)-Coniines and (-)-Sedamine by Diastereoselective Alkylation Reaction of Ethoxypiperidinone

Toshiko Kiguchi, Yoko Nakazono, Sanae Kotera, Ichiya Ninomiya, and Takeaki Naito*

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


Diastereoselective alkylation reaction of the chiral 6-ethoxypiperidinoes (4) and (5) has been developed and successfully applied to the asymmetric synthesis of piperidine alkaloids, (+)- and (-)-coniines (11) and (12), (-)-sedamine (21), and (-)-allosedamine (22).

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Paper | Regular issue | Vol 31, No. 8, 1990, pp. 1537 - 1542
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DOI: 10.3987/COM-90-5453
A New Synthesis of 5,6-Dihydro-4H-1,3,4-thiadiazine 1,1-Dioxides from Methyl Styrylsulfonylacetate

Masahiko Takahashi* and Ichiro Yamashita

*Department of Industrial Chemistry, Faculty of Engineering, Ibaraki University, 4-12-1 Nakanarusawamachi, Hitachi, Ibaraki 316-8511, Japan


Treatment of methyl styrylsulfonylacetate with arenediazonium chloirdes gave methyl styrylsulfonylglyoxylate arenehydrazones, which were cyclized on treatment with bases to 4-aryl-5-phenyl-5,6-dihydro-1,3,4-thiadiazine 1,1-dioxides, a hitherto unknown class of heterocycles.

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Paper | Regular issue | Vol 31, No. 8, 1990, pp. 1543 - 1548
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DOI: 10.3987/COM-90-5459
Stereoselective Synthesis of 1-Indanylidene Substituted Heteroaromatic Derivatives via Pd-catalyzed Tandem Insertion and Cross Coupling Reactions

Fen-Tair Luo* and Ren-Tzong Wang

*Institutue of Chemistry, Academia Sinica, 128, Yan-Chiu-Yuan Road, Sec II, Nankang, Taipei,11529, Taiwan, R.O.C.


Treatment of 4-(o-iodophenyl)-1-butyne with a variety of heteroarylzinc chlorides in the presence of a catalytic amount of Pd(PPh3)4 gave (Z)-1-indanylidene substituted heteroaromatics in moderate to good yields with high Z-selectivities.

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Paper | Regular issue | Vol 31, No. 8, 1990, pp. 1549 - 1554
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DOI: 10.3987/COM-90-5466
A Practical Approach to the Synthesis of 1,2,3,4,6,7,8,9-Octahydro-1,3-dimethylprimido[2,1-f]purine-2,4,8-trione

Vivekanand Kamath, Jahangir, and David C. Baker*

*Department of Chemistry, University of Alabama, Box 870336, University, Tuscaloosa, Alabama 35478-0336, U.S.A.


A practical synthesis of 1,2,3,4,6,7,8,9-octahydro-1,3-dimethylpyrimido[2,1-f]purine-2,4,8-trione, which obviates difficulties encountered in exeuting th epublisehd method, is described.

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Paper | Regular issue | Vol 31, No. 8, 1990, pp. 1555 - 1563
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DOI: 10.3987/COM-90-5476
Practical Route to Both (S)- and (R)-Enantiomers of O-(4-Methoxyphenyl)glycidol Using (S)-1,2-O-Isopropylideneglycerol as a Common Precursor

Seiichi Takano,* Minoru Moriya, Mahito Suzuki, Yoshiharu Iwabuchi, Takumichi Sugihara, and Kunio Ogasawara

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


Practical route to both (R)- and (S)-enantiomers of O-(4-methoxyphenyl)glycidol is devised using (S)-1,2-O-isopropylideneglycerol as a common chiral starting material.

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27 data found. 1 - 27 listed