Regular Issue

Vol. 22, No. 2, 1984

32 data found. 1 - 30 listed Next Last
Communication | Regular issue | Vol 22, No. 2, 1984, pp. 223 - 227
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DOI: 10.3987/R-1984-02-0223
An Elegant Synthesis of 2,2-Dimethyl-2H,5H-pyrano[3,2-c][1]benzopyran-5-ones

V. K. Ahluwalia,* K. K. Arora, and Irani Mukherjee

*Department of Chemistry, University of Delhi, Delhi-110 007, India


Title compounds have been synthesised by the condensation of 4-hydroxycaumarins with isoprene followed by dehydrogenation with DDQ.

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Communication | Regular issue | Vol 22, No. 2, 1984, pp. 229 - 231
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DOI: 10.3987/R-1984-02-0229
The Recation of 4-Hydroxy-2H-1-benzopyran-2-ones with But-1,3-diene and But-3-en-2-ol

V. K. Ahluwalia,* Irani Mukherjee, and Rishi P. Singh

*Department of Chemistry, University of Delhi, Delhi-110 007, India


The reaction of 4-hydroxy-2H-1-benzopyran-2-ones with but-1,3-diene or with but-3-en-2-ol in presence of orthophosphoric acid afforded 3-(but-2’-enyl)-4-hydroxy-2H-1-benzopyran-2-ones. The structures of the compounds have been established spectroscopically.

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Communication | Regular issue | Vol 22, No. 2, 1984, pp. 233 - 236
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DOI: 10.3987/R-1984-02-0233
Convenient Synthesis of 6,7-Dihydroflavopereirine and Flavopereirine

Venkatachalam S. Giri, Bhim C. Maiti, and Satyesh C. Pakrashi*

*Indian Institute of Chemical Biology, Calcutta-700 032, India


The alkaloids 6,7-dihydroflavopereirine (9) and flavopereirine (10) have been synthesised from 3-acetyl-4-oxo-6,7-dihydro-12H-indolo[2,3-a]quinolizine (5) obtained in one step by condensation of 1-methyl- 3,4-dihydro-β-carboline (3) and ethyl ethoxymethyleneacetoacetate (4).

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Communication | Regular issue | Vol 22, No. 2, 1984, pp. 237 - 240
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DOI: 10.3987/R-1984-02-0237
Asymmetric Photocyclization of N-α,β-Unsaturated Acylanilides

Takeaki Naito, Yukiko Tada, and Ichiya Ninomiya*

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


Photocyclization of the acylanilides (1a and b) and (3a and b) in the presence of a chiral dibasic acid yielded the optically active quinolones (2a and b), (4b), and (5a and b) with optical yields ranging from 12 to 42 %.

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Communication | Regular issue | Vol 22, No. 2, 1984, pp. 241 - 244
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DOI: 10.3987/R-1984-02-0241
The Friedel-Crafts Acylation of Ethyl Indole-2-carboxylate. An Unusual Substitution on the Benzene Moiety

Yasuoki Murakami,* Masanobu Tani, Kenjiro Tanaka, and Yuusaku Yokoyama

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


Ethyl indole-2-carboxylate can be acylated with a variety of acyl chlorides under Friedel-Crafts conditions to give mono-acyl indole derivatives. However, the acyl chloride derived from a stronger acid tends to substitute at the C-5 position rather than at the C-3, a usual nucleophilic center of indoles.

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Communication | Regular issue | Vol 22, No. 2, 1984, pp. 245 - 248
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DOI: 10.3987/R-1984-02-0245
Oxygen Heterocycles by Sulphur Ylide Annulation: Synthesis of 3,4-Dihydro-2H,5H-pyrano[3,2-c][1]benzopyran-5-ones by Dimethylsulphoxonium Methylide

Pierfrancesco Bravo,* Paola Carrera, Giuseppe Resnati, Calimero Ticozzi, and Giancarlo Cavicchio

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


3,4-Dihydro-2-hydroxymethyl-2H,5H-pyrano[3,2-c][1]benzopyran-5-ones are the main products of the reaction of dimethylsulphoxonium methylide on Michael adducts of 4-hydroxycoumarins and α,β-unsaturated ketones. Minor quantities of 3,4-dihydro-2-hydroxymethyl-2H,5H-pyrano[2,3-b][1]benzopyran-5-ones are also sometimes obtained.

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Communication | Regular issue | Vol 22, No. 2, 1984, pp. 249 - 252
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DOI: 10.3987/R-1984-02-0249
Flemiculosin, a Novel Chalcone from Flemengia fruticulosa

Parth Sarathi Khattri, Mahendra Sahai, Biswanath Dasgupta, and Anil B. Ray*

*Department of Medical Chemistry, Institute of Medical Chemistry, Banaras Hindu University, Varanasi-221 005, India


Flmeiculosin, a novel chalcone isolated from the leaves of Flemngia fruticulose Wall, has been shown to possess an angular benzodipyran system, and its structure has been advanced as 1 on the basis of detailed spectroscopic evidence.

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Communication | Regular issue | Vol 22, No. 2, 1984, pp. 253 - 256
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DOI: 10.3987/R-1984-02-0253
Total Synthesis of Sen-215 by Use of Palladium Catalyzed Carbonylation

Miwako Mori, Minoru Ishikura, Toshihito Ikeda, and Yoshio Ban

*Faculty of Pharmaceutical Sciences, Hokkaido University, Kita 12 Nishi 6, Kita-ku, Sapporo, Hokkaido 060-0812, Japan


The total synthesis of SEN-215 was achieved by use of palladium catalyzed carbonylation.

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Communication | Regular issue | Vol 22, No. 2, 1984, pp. 257 - 260
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DOI: 10.3987/R-1984-02-0257
The Synthesis of C-13 Labeled Vitamin E, [8‘a-13C]all-rac-α-Tocopherol

Shiro Urano,* Kukimo Tokuzawa, Shun-ichiro Nakano, and Mitsuyoshi Matsuo

*Tokyo Metropolitan Institute of Gerontology, 35-2 Sakae-cho, Itabashi-ku, Tokyo 173-, Japan


Vitamin E with a 13c-labeled isoprenoid side chain, [8‘a- 13C]all-rac-α-tocopherol (1), was synthesized using 6-methoxymethoxy- 2,5,7,8-tetramethyl-2-(5-mercaptothiazolinyl-4-methyl-3-penten-1-yl)chroman (8) as a key intermediate and [13C]methyl iodide as a 13C source. The total yield of the labeled tocopherol based on [13C]methyl iodide was 51.2%.

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Communication | Regular issue | Vol 22, No. 2, 1984, pp. 261 - 264
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DOI: 10.3987/R-1984-02-0261
Syntheses of Licoricone and Its Isomer

Masao Tsukayama,* Kunihiro Fujimoto, Tokunaru Horie, Mitsuo Masumura, and Mitsuru Nakayama

*Department of Chemical Science and Technology, Faculty of Engineering, University of Tokushima, Minamijosanjima-cho, Tokushima 770-8506, Japan


The condensation of 6’,7-dibenzoyloxy-2’,4’- dimethoxyisoflavone with 2-methyl-3-buten-2-ol, followed by the hydrolysis of the resultant 3’-(3-methyl-2-butenyl)isoflavone afforded licoricone. Its isomer, 5’-(3-methyl-2-butenyl)isoflavone, was also synthesized from 7-benzoyloxy or 6’,7-dibenzoyloxyisoflavone in a similar manner.

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Communication | Regular issue | Vol 22, No. 2, 1984, pp. 265 - 268
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DOI: 10.3987/R-1984-02-0265
A Convenient Synthesis of 3-Arylpyridines by the Palladium Catalyzed Coupling Reaction of Diethyl(3-pyridyl)borane with Aryl Halides

Minoru Ishikura, Machiko Kamada, and Masanao Terashima*

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


The utilization of heteroarylborane to the preparation of a variety of 3-arylpyridines by the palladium catalyzed cross coupling reaction between diethyl(3-pyridyl)borane and aryl halides in the presence of bases is described.

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Communication | Regular issue | Vol 22, No. 2, 1984, pp. 269 - 270
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DOI: 10.3987/R-1984-02-0269
A Facile Route to 3,4-Synnetrically Substituted 2-Carbethoxy-5-methylpyrroles

Peter D. Williams and Eugene LeGoff*

*Department of Chemistry, Michigan State University, East Lansing, MI 48824, U.S.A.


A synthesis of 3,4-disubstituted 2-carbethoxy-5-methylpyrroles from alkenes via isoxazoles is described.

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Communication | Regular issue | Vol 22, No. 2, 1984, pp. 271 - 274
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DOI: 10.3987/R-1984-02-0271
Synthesis and Thermal Rearrangement of 5-Chiloro-4,6-dinitrobenzofuroxan

William P. Norris* and Andrew Chafin

*Research Department, Naval Weapons Center, China Lake, CA 93555, U.S.A.


5-Chloro-4,6-dinitrobenzofuroxan, prepared by nitration of 5-chlorobenzofuroxan, isomerizes thermally to 7-chloro-4,6-dinitrobenzofuroxan. The latter compound reacts with water, in the presence of potassium bicarbonate, to give the potassium salt of 7-hydroxy-4,6-dinitrobenzofuroxan and with methanol, in the presence of potassium bicarbonate, to give potassium 4,7-dihydro-4,6-dinitro-7,7-dimethoxybenzofuroxanide.

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Communication | Regular issue | Vol 22, No. 2, 1984, pp. 275 - 276
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DOI: 10.3987/R-1984-02-0275
Synthesis of Tetrahydroquinoline Derivatives by [4+2]Cycloaddition Reaction

Tetsuji Kametani,* Hajime Takeda, Yukio Suzuki, and Toshio Honda

*Hoshi University, 2-4-41 Ebara, Shinagawa-ku, Tokyo 142-8501, Japan


Teterahydroquinoline derivatives (4 and 5) were synthesized by Lewis acid catalyzed [4+2]cycloaddition reaction of the olefins (1 and 2) and the imine (3).

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Communication | Regular issue | Vol 22, No. 2, 1984, pp. 277 - 280
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DOI: 10.3987/R-1984-02-0277
Reactions of 4-Acetoxy-2H-1,4-benzthiazin-3(4H)-one

Norio Kugai, Yuichi Hashimoto, and Koichi Shudo*

*Faculty of Pharmaceutical Sciences, University of Tokyo, Hongo, Bunkyo-ku, Tokyo 113, Japan


4-Acetoxy-2H-1,4-benzthiazin-3(4H)-one (5), a unique arylhydroxamic acid derivative, reacted with some nucleophiles. The position 2 of compound 5 is the center of high reactivity, and even benzene reacted with 5 nucleophilically at the position.

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Communication | Regular issue | Vol 22, No. 2, 1984, pp. 281 - 286
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DOI: 10.3987/R-1984-02-0281
Bis Heteroannulation. 6. The First Example of a Deils-Alder Reaction Involving a Thiazole Ring with an Acetylenic Dienophile. Geometrical Control of Reaction Pathway

Peter A. Jacobi,* Kim T. Weiss, and Melissa Egbertson

*Hall-Atwater Laboratories, Wesleyan University, Middletown, Connecicut 06459-0180, U.S.A.


Acetylenic thiazoles of proper design have been shown to undergo an intramolecular Diels-Alder reaction leading directly to fused-ring thiophene derivatives.

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Report | Regular issue | Vol 22, No. 2, 1984, pp. 287 - 293
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DOI: 10.3987/R-1984-02-0287
Azlactones in Heterocyclic Synthesis: Reaction of δ2-Oxazolin-5-one with Furylacrolein Anils

Dipak Prajapati, Jagir Singh Sandhu,* Jogendra Nath Baruah, Tetsuji Kametani, Hiromasa Nagase, Kenichi Kawai, and Toshio Honda

*Division of Drug and Pharmaceutical Chemistry, Regional Research Laboratory, Jorhat 785 006, Assam, India


Reaction of furylacrolein anils with mesoionic oxazolin-5-one gave α-pyridones and there was no evidence for the formation of β-lactams. The pyridone structures were fully supported by spectral data and the X-ray analysis of (4b).

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Report | Regular issue | Vol 22, No. 2, 1984, pp. 295 - 298
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DOI: 10.3987/R-1984-02-0295
Studies on the Chemical Constituents of Azadirachta indica A. Juss (Meliaceae) Part I: Isolation and Structure of a New Tetranortriterpenoid — Nimolicinol

Salimuzzaman Siddiqui,* Shaheen Faizi, and Bina S. Siddiqui

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


A new tetranortriterpenoid provisionally named as nimolicinol has been isolated from the fresh, ripe, undried fruits of Azadirachta indica A. Juss (Neem) and its structure has been elucidated as 17α-hydroxy-14,15-deoxy-17-epi-gedunin (I) by spectral studies.

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Report | Regular issue | Vol 22, No. 2, 1984, pp. 299 - 301
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DOI: 10.3987/R-1984-02-0299
Synthesis of 9H-Pyrrolo[1,2-a]-1,4-diazaindol-9-one

Daniel Ladurée, Hussein El Kashef, and Max Robba*

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


The synthesis of 9H-pyrrolo[1,2-a]-1,4-diazaindol-9-one was achieved either by an intramolecular electrophilic substitution of 2-chlorocarbonyl-3-N-pyrrolopyrazine 7 and 2-N-pyrrolidinocarbonyl-3-N-pyrrolopyrazine 8 or by the intramolecular nucleophilic substitution of 2-chloro-3-(2-pyrrolyl)pyrazine 12.

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Report | Regular issue | Vol 22, No. 2, 1984, pp. 303 - 305
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DOI: 10.3987/R-1984-02-0303
Synthesis of 5H-Pyrrolo[1,2-a]-1-azaindole and Derivatives

Daniel Laudurée and Max Robba*

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


The synthesis of 5H-pyrrolo[1,2-a]-1-azaindol-5-one was achieved by intramolecular nucleophilic displacement of 2-chloro-3-(2-pyrrolylcarbonyl)pyridine. The reduction of the latter gave either 5H-pyrrolo[1,2-a]-1-azaindol-5-ol or 5H-pyrrolo[1,2-a]-1-azaindole.

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Report | Regular issue | Vol 22, No. 2, 1984, pp. 307 - 310
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DOI: 10.3987/R-1984-02-0307
The Stereoselective Oxidation of 1-Benzylnicotinium Bromide to Its 1‘-N-Oxide

Makoto Shibagaki,* Hajime Matsushita, and Hajime Kaneko

*Life Science Research Laboratory, Japan Tobacco Inc., 6-2, Umegaoka, Midori-ku, Yokohama, Kanagawa 227-8512, Japan


1’-N-oxidation of 1-benzylnicotinium bromide(4) was studied. Among the oxidizing agents examined, peroxomolybdate and peroxotungstate gave the cis- and trans-1’-N-oxides(5 and 6) in the ratio of 1 : 14 and 1 : 15, respectively.

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Report | Regular issue | Vol 22, No. 2, 1984, pp. 311 - 331
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DOI: 10.3987/R-1984-02-0311
Benzo- and Indoloquinolizidine Derivatives XIX. The Synthesis and Pharmacologocal Activity of Some Quinolizidine Derivatives, Analogues of Butaclamol

G. Laus, D. Tourwé, and G. Van Binst*

*Laboratoium voor organische Chemie, Vrije Universiteit Brussel, Pleinlaan 2, B-1050 Brussel, Belgium


Indenopyridoisoquinoline and benzopyridophenanthridine derivatives were synthesized as the conformationally rigid analogues of butaclamol. For both series, a unique reaction scheme has been worked out in order to obtain the desired trans-cisoid-cis conformation of the end products. In this conformation, the indenopyridoisoquinoline derivative simulates the proposed active form of butaclamol, whilst the benzopyridophenanthridine derivatives simulate the non-active form of butaclamol. The products were tested for neuroleptic activity in “in vitro” models. No significant binding was detected. In view of the pharmacological assays, we cannot decide about the correctness of the proposed structure-activity relationship in the butaclamol series. Overall topological congruence of the phenethylamine part and some flexibility of the system may be important factors for activity.

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Report | Regular issue | Vol 22, No. 2, 1984, pp. 333 - 337
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DOI: 10.3987/R-1984-02-0333
Bhubaneswin: A New Bicoumarin

Sudam C. Basa,* Surga P. Das, Rabindra N. Tripathy, Varadaraj Elango, and Maurice Shamma

*Regional Research Laboratory, Bhubaneswar 751 013, India


The new bicoumarin bhubaneswin (3) has been obtained from Boenninghausenia albiflora Reichb. ex Meissner (Rutaceae).

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Report | Regular issue | Vol 22, No. 2, 1984, pp. 339 - 344
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DOI: 10.3987/R-1984-02-0339
Synthesis of 3-Halo- and 3-Formyl-4-alkylpyridines

Daniel L. Comins,* Roy K. Smith, and Eric D. Stroud

*Department of Chemistry abd Biochemistry, Utah State University, Logan, Utah 84332-0300, U.S.A.


In the presence of a catalytic amount of cuprous iodide, the addition of Grignard reagents to the 1-phenoxycarbonyl salts of 3-halopyridines gives 4-alkyl-3-halo-1-phenoxycarbonyl-1,4-dihydropyridines. The crude dihydropyridines were aromatized with o-chloranil to give 4-alkyl-3-halopyridines. Several 4-alkylnicotinaldehydes were synthesized in a similar manner from the cyclic acetal (1,3-dioxolane) of 3-pyridinecarboxaldehyde. After aromatization with sulfur, the crude acetals were hydrolyzed with oxalic acid to give the desired pyridinecarboxaldehydes.

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Report | Regular issue | Vol 22, No. 2, 1984, pp. 345 - 351
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DOI: 10.3987/R-1984-02-0345
Syntheis of 3-Amino-2-carbamimidoylpyrazole C-Nucleosides and Its Cyclization to 4-Aminopyrazolo[1,5-a]-1,3,5-triazine C-Nucleosides

Chung K. Chu*

*Department of Medical Chemistry and Pharmacognosy, College of Pharmacy, The University of Georgia, Athens, Georgia 30602, U.S.A.


4-Amino-8-(β-D-2,3-O-isopropylidene-5-O-tritylribofuranosyl)pyrazolo[l,5-a]-1,3,5-triazine and its α-isomer were synthesized via 3-amino-2N-carbamimidoyl-4-(α and β-D-2‘,3‘-O-isopropylidene-5‘-O-tritylribofuranosyl)pyrazoles.

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Report | Regular issue | Vol 22, No. 2, 1984, pp. 353 - 354
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DOI: 10.3987/R-1984-02-0353
Heterosysles in Organic Synthesis. Part VI — A Facile Synthesis of 1-(4-Aryl-2-thiazolyl)-2-propanones

Harjit Singh,* Sunil K. Aggarwal, and Nageshwar Malhotra

*Department of Chemistry, Guru Nanak Dev University, Amritsar -143 005, Punjab, India


Reactions of ω-(6-methyl-4-pyrimidinylthio)acetophenones (1) with aq. HCl/HClO4 or POCl3 followed by hydrolysis provide 1-(4-aryl-2-thiazolyl)-2-propanones (3).

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Report | Regular issue | Vol 22, No. 2, 1984, pp. 355 - 364
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DOI: 10.3987/R-1984-02-0355
A Facile 2,6-Transannular Cyclisation of 2-Aryl-1,2,4,5-tetrahydro-1-benzazocine-3,6-diones from 1,2-Bis(trimethylsilyloxy)cyclobutene and Schiff Bases

Latchezar S. Trifonov and Alexander S. Orahovats*

*Centre of Ohyrochemistry, Institute of Organic Chemistry, Bulgarian Academy of Sciences, 1113 Sofia, Bulgaria


Tetrahydroquinolines 3 formed via addition of 1,2-bis(trimethylsilyloxy)cyclobutene to Schiff bases afford on oxidative cleavage 2-aryl-1,2,4,5-tetrahydro-1-benzazocine-3,6-diones 5. The latter under mild conditions cyclise 2,6-transannularly to indolin-3-ones 4.

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Report | Regular issue | Vol 22, No. 2, 1984, pp. 365 - 369
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DOI: 10.3987/R-1984-02-0365
Pyranoisoxazole Systems. Synthesis of 3-Oxo-6,7-dihydro-3H,7aH-pyrano[4,3-c]isoxazoles and 4-Oxo-3,6,6-trimethyl-3a,6,7,7a-tetrahydro-4H-pyrano[4,3-c]isoxazole

Bernard Chantegrel, Abdel Ilah Nadi, and Suzanne Gelin*

*Département de Biochimie, Laboratoire de Chimie Organique, Institut National des Sciences Appliquées, 20 Avenue Albert Einstein 69621 Villeurbanne Cedex, France


The reaction of hydroxylamine with 2,3-dihydropyran-4-ones provides a route to 3-oxa-6,7-dihydro-3H,7aH-pyrano[4,3-c]isoxazole derivatives. In addition, the spectral properties of a representative series of the three possible isomeric isoxazoles having a fused-pyran ring was investigated.

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Report | Regular issue | Vol 22, No. 2, 1984, pp. 371 - 374
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DOI: 10.3987/R-1984-02-0371
A Development of Pictet-Spengler Reaction in Aprotic Media Using Chloroformates; a Short Synthesis of Borrerine

Etsuji Yamanaka, Naoki Shibata, and Shin-ichiro Sakai*

*Faculty of Pharmaceutical Sciences, Chiba University, 1-33 Yayoi-cho, Inage-ku, Chiba 263-8522, Japan


Pictet-Spengler reaction between tryptamine (1) and aldehydes (2a,b) was achieved through the intermediates (5a,b,c) in the presence of chloroformates to give the β-carbolines (6a,b,c), which were converted to the amines (7a,b) and the natural alkaloid, borrerine (8).

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Report | Regular issue | Vol 22, No. 2, 1984, pp. 375 - 378
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DOI: 10.3987/R-1984-02-0375
A Novel Synthesis of a 2-Thioxopenam

Ute Krahmer-Seifert and Gerhard Emmer*

*Sandoz Forschungsinstitut, 1235 Wien, Brunnerstraße 59, Austria


The synthesis of an optically active 2-thioxopenam through thermal rearrangement of a 2-t-butylsulfinylpenem to a penemsulfenic acid intermediate and its in situ deoxygenation is described.

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32 data found. 1 - 30 listed Next Last