Regular Issue

Vol. 29, No. 6, 1989

26 data found. 1 - 26 listed
Communication | Regular issue | Vol 29, No. 6, 1989, pp. 997 - 1002
Published online:
DOI: 10.3987/COM-89-4560
Continuing Investigation on the Constituents from Aconitum flavum

Zhi-gang Chen, Ai-na Lao, Hong-cheng Wang, and Shan-hai Hong*

*Shanghai Institute of Material Media, Chinese Academy of Science, 319, Yue-yang Road, Shanghai, 200031, China


The structures of three new C19 diterpenoid alkaloids, flavaconidine (1), N-acetylflavaconitine (2), and flavaconijine (3), isolated in the continuing investigation of Aconitum flavum Hand-Mazz, were determined on the basis of spectroscopic evidence and chemical correlations. They are the first examples of natural diterpenoid alkaloids bearing an acyl instead of usual alkyl group on the nitrogen.

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Communication | Regular issue | Vol 29, No. 6, 1989, pp. 1003 - 1004
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DOI: 10.3987/COM-89-4891
Intramolecular Cycloadditions with Isobenzofurans-VI. A Novel Entry into the Field of Annelated 1,2-Benzisoxazoles

Lutz Assmann and Willy Friedrichsen*

*Institut für Organische Chemie, Universität Kiel, Olshausenstrasse. 40, D-24098 Kiel, Germany


Rh2 OAc4 catalyzed nitrogen extrusion from 5b yields 8 ; this novel route to an annelated isoxazole obviously proceeds through a furo[3,4-d]isoxazole of type 6 as an intermediate.

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Communication | Regular issue | Vol 29, No. 6, 1989, pp. 1005 - 1012
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DOI: 10.3987/COM-89-4900
Reactions of 5-Bromo-2-methoxytropone and 8-Bromo- and 6,8-Dibromocyclohepta[b][1,4]benzoxazines with o-Aminophenol

Tetsuo Nozoe,* Hidetsugu Wakabayashi,* and Sumio Ishikawa

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


Reaction of the title tropone (3) and 8-bromo compound (19) with o-aminophenol (4) in acetic acid affords the HBr salt of 8-(o-hydroxyanilino)cyclohepta[b][1,4]benzoxazine (21) as the main product, whereas under basic conditions treatment of 19 with 4 results in the formation of mainly 2- and 3-formylphenoxazine. Reaction of 6,8-dibromo compound 20 with 4 produces various tropylium compounds having two annulated heterocycles. Possible reaction pathways involving unusual intramolecular transpositions of heterocycles are discussed.

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Communication | Regular issue | Vol 29, No. 6, 1989, pp. 1013 - 1016
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DOI: 10.3987/COM-89-4945
Palladium-catalyzed Indole and Benzofuran Ring Formation Accompanying Carbonylation

Yoshinori Kondo, Takao Sakamoto, and Hiroshi Yamanaka*

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


The reaction of 2-(1-hexynyl)aniline with carbon monoxide in methanol under basic conditions is promoted by the catalytic action of palladium dichloride to give methyl 2-butylindole-3-carboxylate. Similarly, the reaction of 2-(1-hexynyl)phenol under the same conditions gives methyl 2-butylbenzofuran-3-carboxylate. The carbonylative cyclization mentioned above is successful with the corresponding 2-phenylethynyl derivatives of aniline and phenol .

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Communication | Regular issue | Vol 29, No. 6, 1989, pp. 1017 - 1021
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DOI: 10.3987/COM-89-4948
New C19-Diterpenoid Alkaloids from Delphinium nuttallianum Pritz

Yili Bai, Michael Benn,* and Walter Majak

*Department of Chemistry, The University of Alberta, Calgary, Alberta, T2N, 1N4, Canada


Sixteen known and four apparently novel C19-diterpenoid alkaloids were isolated from D. nuttallianum and their structures were determined by eims, 1Hand I3C nmr.

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Communication | Regular issue | Vol 29, No. 6, 1989, pp. 1023 - 1027
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DOI: 10.3987/COM-89-4958
Total Synthesis of AK-Toxin II

Kenshi Ando, Takae Yamada, Yoshihisa Takaishi, and Masayuki Shibuya*

*Faculty of Pharmaceutical Sciences, University of Tokushima, Sho-machi 1, Tokushima 770-8505, Japan


Total synthesis of AK-toxin II, a host-specific phytotoxic metabolite, is described using D-fructose as starting material.

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Communication | Regular issue | Vol 29, No. 6, 1989, pp. 1029 - 1032
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DOI: 10.3987/COM-89-4962
Ctystallographic Evidence of Stereoselective exo-Cycloaddition for 1,3-Dipolar Reaction of 3,5-Dimethypyridine N-oxide with N-Substituted Maleimides and Some Comments

Kazunobu Harano, Toshikazu Matsuoka, Masashi Eto, Tatsuya Matsuzaki, and Takuzo Hisano*

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


The crystal structure of the 1,5-sigmatropic rearrangement product of the cycloadduct of 3,5-dimethylpyridine N-oxide and N-butylmaleimide was elucidated. The result indicates that the cycloaddition proceeds via exo transition state.

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Communication | Regular issue | Vol 29, No. 6, 1989, pp. 1033 - 1035
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DOI: 10.3987/COM-89-4978
Syntheses of an Alkaloid, (±)-3-Demethoxyerythratidinone

Hiroshi Irie,* Kuniyo Shibata, Kouya Matsuno, and Yong Zhang

*Faculty of Pharmaceutical Sciences, Nagasaki University, 1-14, Bunkyo-machi, Nagasaki 852-8521, Japan


Synthesis of (±)-3-demethoxyerythratidinone, one of the simple erythrina-alkaloids, was accomplished by application of an intramolecular Wittlg reaction for constructing α, β-unsaturated five membered lactam as a key step.

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Communication | Regular issue | Vol 29, No. 6, 1989, pp. 1037 - 1040
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DOI: 10.3987/COM-89-5015
Structure and Absolute Configuration of the Ochrosia Alkaloid Ochromianine: Syntheses of (±)- and (—)-Ochromianine

Tozo Fujii,* Masashi Ohba, Takeshi Tachinami, Takako Ohashi, Michel Koch, and Elisabeth Seguin

*Faculty of Pharmaceutical Scicences, Kanazawa University, 13-1 Takara-machi, Kanazawa 920-0934, Japan


The structure of the Ochrosia alkaloid ochromianine has been established as 11-methoxydihydrocorynantheol [(-)-I] as a result of the racemic and chiral syntheses of the candidate structure I. These syntheses started from the lactim ethers (±)-III and (+)-III, respectively, and proceeded through the intermediates (±)-IV, (±)-VI, and (±)-VIII and through (+)-IV, (+)-VI, and (-)-VIII, respectively.

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Paper | Regular issue | Vol 29, No. 6, 1989, pp. 1041 - 1064
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DOI: 10.3987/COM-89-4762
Electron Transfer - Induced Photochemical Reactions in Imide- RXCH2 TMS Systems. Photoaddition of α-Trimethylsilyl Substituted Heteroatom Containing Compounds to Phthalimides

Ung-Chan Yoon,* Hyun-Jin Kim, and Patrick S. Mariano

*Department of Chemistry , College of Natural Sciences, Pusan National University, Kumjeong-ku, Pusan 609-735, Korea


Studies have been conducted to explore single electron transfer (SET) induced photoaddition reactions of phthalimides with the α-silyl-n-electron donors (EtOCH2TMS, n-PrSCH2TMS and Et2NCH2TMS). Photoadditions of EtOCH TMS, n-PrSCH2TMS and Et2NCH2TMS to phthalimides in CH3CN or CH3OH occur in moderate to high yields to produce 3-substituted phthalimidines. The primary photoadducts undergo dehydration (or desilanolation) to generate 3-alkylidenylphthalimidine derivatives by pathways which are accelerated by acid impurity. Mechanisms for these photoadditions involving SET from α-silyl-n-electron donors to excited phthalimides followed by selective desilylation of the intermediate cation redicals and radical coupling are proposed.

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Paper | Regular issue | Vol 29, No. 6, 1989, pp. 1065 - 1076
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DOI: 10.3987/COM-89-4769
Fused Heterocyclic System. Note I. Pyrano[3,4-c]pyrrole-4,7(2H.6H)-dione. Synthesis and General Pharmacological Screening

Sergio Caronna, Liliana Lamartina, Salvatore Petruso, Vincenzo Spiro, Antonina Caruso, and Antonio Felice

*Tecnologie Farmaceutiche, Dipartimento di Chimica, Università digli Studi di Palermo, Via Archirafi 32, 90123 Palermo, Italy


A general synthesis of pyrano[3,4-c]pyrrole-4,7(2H,6H)-dione derivatives is described. The structures of epoxypropyl intermediates and of final compounds are demonstrated by 13C-nmr analysis. There are also reported the results of a general pharmacological screening on the compounds of the title.

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Paper | Regular issue | Vol 29, No. 6, 1989, pp. 1077 - 1090
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DOI: 10.3987/COM-89-4836
Preparation of 4-Amino-3(2H)-pyridazinones by Direct Amination of 3(2H)-Pyridazinones with Hydrazine

William J. Coates and Alexander McKillop

*Smith Kline & French Research Ltd., The Frythe, Welwyn, Hertfordshire, AL7 1EX, U.K.


Reaction of a variety of 3(2H)-pyridazinones with hydrazine hydrate gives moderate to excellent yields of the corresponding 4-amino-3(2H)-pyridazinones.

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Paper | Regular issue | Vol 29, No. 6, 1989, pp. 1091 - 1095
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DOI: 10.3987/COM-89-4856
A New Isoquinoline Alkaloid Papraine from Fumaria indica

Atta-ur-Rahman,* Mohammad Khalid Bhatti, Hussain Ahmad, Habib-ur-Rahman, and David S. Rycroft*

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


A new phthalide isoquinoline alkaloid (+)-papraine (1) has been isolated from Fumaria indica and its structure and absolute configuration have been assigned.

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Paper | Regular issue | Vol 29, No. 6, 1989, pp. 1097 - 1105
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DOI: 10.3987/COM-89-4889
A One-pot Formation of the Analogues of Cherylline- and Latifine-type 4-Aryl-1,2,3,4-tetrahydroisoquinolines

Masaru Kihara,* Seiichiro Iguchi, Yasuhiro Imakura, and Shigeru Kobayashi

*Pharmaceutical Sciences, Graduate of School, University of Tokushima, Sho-machi, Tokushima 770-8505, Japan


The cyclization reaction of N-(2-bromo-4,5-dimethoxybenzyl)-1-(4-methoxyphenyl) -2-aminoethanol (9) with conc. H2SO4, 80% H2SO4, or conc. HC1-benzene yielded cherylline analogues (5) and/or (6) along with latifine analogues (7) and/or (8) according to the biogenetic route.

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Paper | Regular issue | Vol 29, No. 6, 1989, pp. 1107 - 1118
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DOI: 10.3987/COM-89-4895
C(2)-Carboxy and Carboxymethyl Cephems

Douglas O. Spry,* Nancy J. Snyder, David A. Preston, and Chyun-Yen E. Wu

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


A series of C(2)-substituted [methyl, carboxy and carboxymethyl] cephems have been prepared. Test data show a significant reduction in antiblotic activity. Penicillin binding protein (PBP) studies show a decreased affinity to essential PBP-3 in S. aureus X1.1 and E. coli K12. The effect is believed to be steric in nature.

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Paper | Regular issue | Vol 29, No. 6, 1989, pp. 1119 - 1125
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DOI: 10.3987/COM-89-4899
Constituents of Dragon’s Blood. Part III. Dracooxepine, a Novel Type of Biflavanoid

Alberto Arnone, Gianluca Nasini,* and Lucio Merlini

*Dipartmento di Chimica del Polotecnico, Centro Studio Sostanze Organiche Naturali, C.N.R., Piazza Leonardo da Vinci 32, 20133 Milano, Italy


From “Dragon’s blood” resin (from Daemonorops draco Blume) a new biflavanoid with an unusual benzodionepine moiety was isolated. Its structure was established by chemical and spectroscopic means. A possible mechanism of formation in the resin is proposed.

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Paper | Regular issue | Vol 29, No. 6, 1989, pp. 1127 - 1135
Published online:
DOI: 10.3987/COM-89-4905
Isolation, Structure Elucidation, and Synthesis of the Major Anaerobic Bacterial Metabolite of the Dietary Carcinogen 2-Amino-3,4-dimethyl-3H-imidazo[4,5-f]quinoline (MeIQ)

Mohammad Bashir, David G. I. Kingston,* Robert J. Carmen, Roger L. Van Tassell, and Tracy D. Wilkins*

*Department of Chemisry, Virginia Polytecnic Institute and State University, Blacksburg, Virginia 24061-0212, U.S.A.


Incubation of the heterocyclic cooked food mutagen 2-amino-3,4-dimethyl-3H-imidazo[4,5-f]quinoline (MeIQ, 3) with mixed human fecal microflora under anaerobic conditions yielded 2-amino-3,6-dihydro-3,4-dimethyl-7H-imidazo[4,5-f]quinolin-7-one (HOMeIQ, 4) as the major detectable metabolite. HOMeIQ (4) was synthesized in six steps from 6-bromo-7-methylquinoline (5).

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Paper | Regular issue | Vol 29, No. 6, 1989, pp. 1137 - 1148
Published online:
DOI: 10.3987/COM-89-4911
Synthssis of 1H-Pyrrolo[1,2-c]imidazoles

Branislav Musicki,* Mary F. Malley, and J. Z. Gougoutas

*The Squibb Institute for Medical Research, P. O. Box 4000, Princeton, N.J. 08540-4000, U.S.A.


A simple method for the preparation of 1H-pyrrolo[1,2-c]imidazole derivatives is described. The title compounds 6a-d were obtained by condensation of 2-formylpyrroles 2a-d with ammonium acetate. The 2-formylpyrroles also condense with other aromatic aldehydes in the presence of ammonium acetate to afford 1H- pyrrolo[1,2-c]imidazoles 6e-h. The structure of 6h was confirmed by single crystal X-ray analysis.

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Paper | Regular issue | Vol 29, No. 6, 1989, pp. 1149 - 1162
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DOI: 10.3987/COM-89-4915
Alkylation and Acylation of 2-Hydroxy-9(10H)-acridinone and 2-Hydroxy-9(10H)-thioacridinone

Djéridi Dhif, Jean-Pieerre Galy,* Emile-Jean Vincent, and Jacquwa Barbe

*Laboratoire de Chimie Organique Physique, Facluté des Sciences et Techniques de Saint Jérôme, Université d’Aix-Marseille III, Avenue Escardille Normandie Niemen (Case 552), 13397 Marseille Cedex 13, France


New compounds, mostly referred as bis(10H)-acridinones and bis-(10H)-thioacridinones, have been prepared from 2-hydroxy-9(10H)-acridinone and 2-hydroxy-9(10H)-thioacridinone. The alkyl-linked derivalives have been prepared under phase transfer catalysis conditions, while the acyl-linked derivatives have been prepared in pyridine by way of tile corresponding acridinyl thallous salts. Some bis-acridines bilinked have been also prepared.

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Paper | Regular issue | Vol 29, No. 6, 1989, pp. 1163 - 1170
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DOI: 10.3987/COM-89-4924
Heterocycles from Nitrile Imines. Part II. Synthesis and Ring-chain Tautomerism of 1,2,3,4-Tetrahydro-s-tetrazines

Ahmad Q. Hussein,* Mustafa M. El-Abadelah, Khalid Al-Adhami, and Ahmad S. Abushamleh

*Chemistry Department, Faculty of Science, University of Jordan, Amman 11942, Jordan


Alkanal methylhydrazones react with nitrile imines to give 1,2,3,4-tetrahydro-s-tetrazines Tetrazines obtained from the reaction of nitrile imines with methylhydrazones of aromatic aldehydes and ketones exhibit ring-chain tautomerism in solution The extent or such tautomerism is influenced both by steric and electronic effects ot substituents.

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Paper | Regular issue | Vol 29, No. 6, 1989, pp. 1171 - 1177
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DOI: 10.3987/COM-89-4932
A Reconfirmation of the Reaction of Glucosyl Isothiocyanate with 2-Chloroethylamine

Haruo Ogura,* Kazuyoshi Takeda, and Hiroaki Takayanagi

*School of Pharmaceutical Sciences, Kitasato University, 5-9-1, Shirokane, Minato-ku, Tokyo 108-8641, Japan


The reaction of tetra-O-acetylglucosyl isothiocyanate (1) with 2-chloroethylamine under basic conditions in aprotic solvent afforded 2-(2’,3’,4’,6’-tetra-O-acetyl-β-D- glucopyranosylamino)-2-thiazoline (2). On the other hand, in Pyridine solution this reaction proceeded to form N, N’-bis(2’,3’,4’,6’-tetra-O-acetyl-β-D-glucopyranosyl)-N-(2-thiazolin-2-yl)thiourea (3). Alkaline hydrolysis of 2 afforded 2-(β-D-glucopyranosylamino)-2-thiazoline (4) as colorless plates, which was confirmed by means of X-ray analysis.

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Paper | Regular issue | Vol 29, No. 6, 1989, pp. 1179 - 1183
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DOI: 10.3987/COM-89-4943
Tris-N,N’,N"’-(3’,4’,5’-trimethoxyphenethyl)-1,3,5-hexahydrotriazine, a Methylenemescaline Trimer: Characterization and Selective Cyclization to Anhalinine under Non-aqueous Conditions

Linda A. Chrisey and Arnold Brossi

*Natural Products Research Center, Department of Chemistry, University of New Brunswick, Bag Service #45222, Fredericton, New Brunswick, E3b 5A3, Canada


The product obtained from the reaction of mescaline with aqueous formaldehyde was assigned the hexahydrotriazine structure 3, on the basis of ms and 1H-nmr spectral data, and microanalysis. Reaction of 3 with hydrochloric acid in aqueous milieu afforded a mixture of anhalinine (2) and mescaline (1), however, exclusively 2 was obtained when the reaction was performed under non-aqueous conditions in glacial acetic acid or in dichloromethane with trifluoroacetic acid.

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Paper | Regular issue | Vol 29, No. 6, 1989, pp. 1185 - 1189
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DOI: 10.3987/COM-89-4954
Facile Synthesis of 2-(5-Isopropyl-5-methyl-4-oxo-2-imidazolin-2-yl)phenyl Phosphonates

Hideyuki Takenaka and Yoshio Hayase

*Aburahi Laboratories, Shionogi & Co. Ltd., Gotanda, Koka-cho, Koka-gun, Shiga 520-3423, Japan


The synthesis of 2-(5-isopropyI-5-methyl-4-oxo-2-imidazoline-2-yl)phenyl phosphonates (3-5) from benzoyl chloride is described. The condensation between benzoyl chloride and 2-amino-2,3-dimethylbutanamide (10) afforded 5-isopropyl-5-methyl-4-oxo-2-imidazolin-2-yl-benzene (11). Lithiation of 11 with sec-butyllithium, followed by reaction with diethyl chlorophosphate gave diethyl 2-(5-isopropyl-5-methyl-4-oxo-2-imidazolin-2-yl)phenylphosphate (3). Treatment of 3 with bromotrimethylsilane afforded 4 and 2-(5-isopropyl-5-methyl-4-oxo-2-imidazolin-2-yl)phenylphosphonic acid (5).

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Paper | Regular issue | Vol 29, No. 6, 1989, pp. 1191 - 1197
Published online:
DOI: 10.3987/COM-89-4955
Stereochemical Studies on 7- and 9-Substitutes 3-Azabicyclo[3.3.1]nonanes (3-ABNs)

Ramasubbu Jeyaraman* and Muthiah Manoharan*

*Department of Chemistry, Bharathidasan University, Tiruchirapalli-620024, India


The conformations and configurations of some 3-azabicyclo[3.3.1]nonane (3-ABN) derivatives are discussed employing C-13 nmr spectral data. The monothioketal of 2,4-diphenyl-3-ABN-9-one exists in chair-chair conformation and has the oxygen axial to the piperidine ring. The product of Reformatsky reaction of the same ABN-9-one has the OH at C-9 to the side of the piperidine ring. The chair-boat conformation is assigned to one of the isomers of 7-methyl-2,4-diphenyl-3-ABN-9-one. The conformations of a few other ABNs are also discussed.

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Paper | Regular issue | Vol 29, No. 6, 1989, pp. 1199 - 1207
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DOI: 10.3987/COM-89-4960
Efficient Olefin Synthesis Using the Pyrazinylsulfunyl Group

Akihiro Ohta,* Yoshiko Tonomura, Hiroko Odashima, Nahoko Fujiwara, and Makoto Shimazaki

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


Ethyl cinnamates, stilbenes and 1,4-diaryl-1,3-butadienes were prepared using the pyrazinylsulfinyl group as a leaving group to affect β-elimination.

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Paper | Regular issue | Vol 29, No. 6, 1989, pp. 1209 - 1216
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DOI: 10.3987/COM-89-4972
Stereoselective Synthesis of (±)-Epilupinine

Tatsuo Nagasaka,* Hiroto Yamamoto, Hideki Hayashi, Hiroki Kato, Miyako Kawaida, Kazuhiro Yamaguchi, and Fumiko Hamaguchi

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


Synthesis of lupin alkaloids starting from 2-piperidinone was attempted by three methods, one of which leads the stereoselective formation of (±)-epilupinine.

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26 data found. 1 - 26 listed