Regular Issue

Vol. 24, No. 12, 1986

25 data found. 1 - 25 listed
Communication | Regular issue | Vol 24, No. 12, 1986, pp. 3337 - 3340
Published online:
DOI: 10.3987/R-1986-12-3337
Ipso-substitution Reaction of 2- and 4-Sulfonylpyridines with Grignard Reagents

Naomichi Furukawa,* Masayuki Tsuruoka, and Hisashi Fujihara

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


The reactions of 2-sulfonylpyridines with Grignard reagents proceeded via an ionic path to give only the corresponding ipso-substitution products, while 4-sulfonylpyridines afforded mainly a mixture of both the substitution and coupling products on treatment with Grignard reagents.

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Communication | Regular issue | Vol 24, No. 12, 1986, pp. 3341 - 3346
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DOI: 10.3987/R-1986-12-3341
Nitriles in Heterocyclic Synthesis: Novel Synthesis of Pyrrole and Pyridine Derivatives

Fathy M. Abdel-Galil, Mohamed M. Sallam, Sherif M. Sherif,* and Mohamed H. Elnagdi

*Department of Chemistry, Faculty of Science, University of Cairo, Giza, Egypt


Synthesis of pyrrolo[3,2-b]pyrrole, pyrrole and pyridine derivatives utilising cyanothioacetamide as starting component is reported.

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Communication | Regular issue | Vol 24, No. 12, 1986, pp. 3347 - 3350
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DOI: 10.3987/R-1986-12-3347
Regioselective Thio-Claisen Rearrangement via S-Allyl Ketene-S,N-acetals Generated from Cyclic S-Allylmonothiodicarboximide Salts

Hiroki Takahata, Yasunori Banba, Mayumi Mozumi, and Takao Yamazaki*

*Faculty of Pharmaceutical Sciences, Toyama Medical and Pharmaceutical University, 2630 Sugitani, Toyama, Toyama 930-0194, Japan


Thio-Claisen rearrangement via S-allyl ketene-S,N-acetals generated from cyclic S-allylmonothiodicarboximide salts with a base furnished the S→C allylic rearranged products exclusively.

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Communication | Regular issue | Vol 24, No. 12, 1986, pp. 3351 - 3358
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DOI: 10.3987/R-1986-12-3351
Demalonylcopiamycin, a New Antibiotic Produced by Streptomyces hygroscopicus var. crystallogenes, the Copiamycin Source

Toshio Fukai, Taro Nomura,* Jun Uno, and Tadashi Arai

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


Demalonylcopiamycin (1) was isolated from the mycelial cake of Streptomyces hygroscopicus var. crystallogenes. The structure was determined by the identification of 1 with alkaline hydrolysis product of copiamycin (2). The new antibiotic (1) was found to be more active against Gram-positive bacteria than copiamycin (2), while slightly more active against fungi.

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Communication | Regular issue | Vol 24, No. 12, 1986, pp. 3359 - 3362
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DOI: 10.3987/R-1986-12-3359
Three New Isoquinoline Alkaloids from Corydalis claviculata (L.) DC.

José Manuel Boente, Domingo Domínguez, and Luis Castedo*

*Facultad de Química y Sección de Alcaloides, Deparamento de Química Orgánica, C. S. I. C., Santiago de Compostela, Spain


We describe the isolation from Corydalis claviculata (L.) DC. and the structure determination of the three new alkaloids dioxocularine 1, norsecocularine 2 and viguine 3.

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Report | Regular issue | Vol 24, No. 12, 1986, pp. 3363 - 3368
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DOI: 10.3987/R-1986-12-3363
Heterocyclization Reactions with Carbodimides: Synthesis of Fused 1,2,4-Triazoles

Pedro Molina,* Mateo Alajarín, and Alicia Ferao

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


Several N-amino heterocycles react with diaryl carbodiimides under neutral conditions to give fused 1,2,4-triazoles. In some cases the intermediate heteroaryl guanidines are isolated, which by thermal or basic treatment cyclized to neutral or mesoionic fused 1,2,4-triazoles.

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Report | Regular issue | Vol 24, No. 12, 1986, pp. 3369 - 3372
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DOI: 10.3987/R-1986-12-3369
A Cyclisation Reaction of 2-Cyanomethylbenzothiazole with Acetylenic Compounds via Michael Addition

Dilip Konwar, Romesh Chandra Boruah, and Jagir Singh Sandhu*

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


2-Cyanomethylbenzothiazole (1) reacts with acetylenic compounds (2) under the influence of base in Michael fashion followed by cyclisation to afford fused pyrido[2,1-b]benzothiazole (3&4) in excellent yields. The products were characterized through elemental and spectral analyses.

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Report | Regular issue | Vol 24, No. 12, 1986, pp. 3373 - 3377
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DOI: 10.3987/R-1986-12-3373
A Useful Construction of 4-Substiotuted 1-Alkylpiperid-3-ones

Charles S. Swindell* and Ruth H. Duffy

*Department of Chemistry, Bryn Mawr College, Bryn Mawr, PA 19010, U.S.A.


A potentially general construction of 4-substituted 1-alkylpiperid-3-ones is described which employs 3-methoxy-4-bromopyridine as the crucial reagent. This substance is coupled at C-4 with Grignard reagents through the Kumada reaction. The resulting pyridines are then N-alkylated and subsequently subjected to borohydride reduction and aqueous acidic hydrolysis to reveal the title piperidones and related substances.

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Paper | Regular issue | Vol 24, No. 12, 1986, pp. 3379 - 3384
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DOI: 10.3987/R-1986-12-3379
New Sesquiterpens from Rzedowskia tolantonguensis (Celastraceae)

Antonio G. González,* Isabel L. Bazzocchi, Angel G. Ravelo, Javier G. Luis, and Xorge A. Domínguez

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


From the aerial part and root bark of Rzedowskia tolantonguensis, six dihydro-β-agarofurane-skeleton sesquiterpenes were isolated. Five were new and identified by spectroscopic methods and chemical reactions.

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Paper | Regular issue | Vol 24, No. 12, 1986, pp. 3385 - 3395
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DOI: 10.3987/R-1986-12-3385
Application of the Lewis Acid Catalyzed [4+2]Cycloaddition Reaction to Synthesis of Natural Quinoline Alkaloids

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

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


Lewis acid catalyzed [4+2]cycloaddition reaction of the Schiff base with the olefin was applied to the syntheses of some natural quinoline alkaloids. The extension of [4+2]cycloaddition using the acetal and the orthoester as dienophiles or using s-triazine derivative as a Schiff base is also described. The electrocyclic reaction of the Schiff base was also examined to synthesize the quinoline compound.

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Paper | Regular issue | Vol 24, No. 12, 1986, pp. 3397 - 3401
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DOI: 10.3987/R-1986-12-3397
Reactions with Chlorosulfonyl/Chlorocarbonyl Isocyanates: Synthesis of Pyrrolo[1,2,3-de]-1,2,4-benzothiadiazin-3(2H)-one 1,1-Dioxides and 1H-Pyrrolo[3,2,1-ij]quinazoline-1,3(2H)-diones

Ahmed Kamal,* Narender A. V. Reddy, and Prahlad B. Sattur

*Regional Research Laboratory, Hyderabad 500 007, India


6-Substituted 2,3-diphenylindoles on reaction with chlorosulfonyl/chlorocarbonyl isocyanates, followed by cyclization with aluminium chloride afforded 9-substituted 5,6-diphenylpyrrolo[1,2,3-de]-1,2,4-benzothiadiazin-3(2H)-one, 1,1-dioxides 2 and 9-substituted 5,6-diphenyl-1H-pyrrolo[3,2,1-ij]quinazoline-1,3(2H)-diones 3 respectively. In these reactions, an electron donating substituent such as methyl group at position 6 in indole is necessary for cyclization.

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Paper | Regular issue | Vol 24, No. 12, 1986, pp. 3403 - 3410
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DOI: 10.3987/R-1986-12-3403
Polycondensed Nitrogen Heterocycles. Part 20. Reactivity of Diazotized 1-(2-Aminophenyl)-pyrroles. Pyrrolo[1,2-f]phenanthridines

Girolamo Cirrincione,* Gaetano Dattolo, Anna Maria Almerico, Giuseppe Presti, and Enrico Aiello

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


Compounds (2) were diazotized under several conditions to prepare pyrrolo[1,2-f]phenanthridines (5). However, together with the Pschorr type cyclization, decomposition and intermolecular coupling reactions were observed.

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Paper | Regular issue | Vol 24, No. 12, 1986, pp. 3411 - 3415
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DOI: 10.3987/R-1986-12-3411
Synthesis and 1,3-Dipolar Cycloaddition of 3-Hydroxy-5-methoxypyridinium N-Imine

Ling-Ching Chen* and Shyh-Chyun Yang

*Graduate Institute of Pharmaceutical Sciences, Kaohsiung Medical University, 100 Shin Chuan 1st Rd., Kaohsiung 80708, Taiwan, R.O.C.


The synthesis and 1,3-dipolar cycloaddition of 3-hydroxy-5-methoxypyridinium N-imine (12) is described. Compound 12 was found to undergo 1,3-dipolar cycloaddition reaction with ethyl propiolate to give ethyl 8-amino-4-methoxy-2-oxo-8-azabicyclo[3.2.1]oct-3,6-diene-6-carboxylate (13) and ethyl 4-hydroxy-6-methoxypyrazo[1,5-a]pyridine-3-carboxylate (14).

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Paper | Regular issue | Vol 24, No. 12, 1986, pp. 3417 - 3421
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DOI: 10.3987/R-1986-12-3417
Studies on Rutaceae: Part IV — Conversion of Atalantin to a Rare Spirotetranortriterpenoid

Julie Banerji,* Lila Nayak, and Biswanath Das

*Chemistry Department, University College of Science, 92 Acharya Prafulla Chandra Road, Calcutta-700009, India


Boron trifluoride etherate treatment of atalantin, the tetranortriterpenoid constituent of Atalantia wightii Tan (Rutaceae), afforded an interesting rearranged epiro-product, the structure of which was confirmed from spectral data.

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Paper | Regular issue | Vol 24, No. 12, 1986, pp. 3423 - 3431
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DOI: 10.3987/R-1986-12-3423
A New Host Specific Toxin from Helminthosporium carbonum

Steven P. Tanis,* Benjamin A. Horenstein, Robert P. Scheffer, and Jack B. Rasmussen

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


The structure and sequence of a new HC-toxin analog 3 produced by H. carbonum is reported.

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Paper | Regular issue | Vol 24, No. 12, 1986, pp. 3433 - 3439
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DOI: 10.3987/R-1986-12-3433
Heterocyclic Rearrangements. Rearrangements of 1,2,4-Oxadiazoles, Isoxazoles, and 1,2,5-Oxadiazoles Involving a Carbethoxythiourea NCS Sequence

Gabriella Macaluso, Giuseppe Cusmano, Silvestre Buscemi, Vincenzo Frenna, Nicolò Vivona,* and Michele Ruccia

*Instituto de Chimica Organica, Facolta de Scienze, Università digli Studi di Palermo, 20 via Archirafi, 90123 Palermo, Italy


The reaction of 3-amino-1,2,4-oxadiazoles 6a,b, 3-aminoisoxazole 9 and 3-amino-1,2,5-oxadiazoles 12a,b with ethoxycarbonyl isothiocyanate has been investigated. In the case of 6a,b, the reaction directly gave the 1,2,4-thiadiazoles 8a,b, because of a spontaneous rearrangement of the initially formed thioureas 7a,b. In the case of 9 and 12a,b, the reaction allowed to isolate the corresponding thioureas which were easily rearranged into 1,2,4-thiadiazoles.

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Paper | Regular issue | Vol 24, No. 12, 1986, pp. 3441 - 3446
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DOI: 10.3987/R-1986-12-3441
Synthesis of Substituted Spiro[azetidin-2-one-4,2’(or 3,2’)-tricyclo[,7]decane] Derivatives

George B. Mullen and Vassil St. Georgiev*

*Department of Organic Chemistry, Pharmaceutical Division, Pennwalt Corporation, Rochester, New York 14623, U.S.A.


The synthesis of two novel adamantane-spiro-azetidin-2-one systems, the spiro[azetidin-2-one-4,2’(or 3,2’)-tricyclo[,7]decanes] 7-10 and 15, respectively), is described.

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Paper | Regular issue | Vol 24, No. 12, 1986, pp. 3447 - 3450
Published online:
DOI: 10.3987/R-1986-12-3447
Ring Openinf of Spiro[azetidin-2-one-4,2’(or 3,2’)-tricyclo[,7]decanes]

George B. Mullen and Vassil St. Georgiev*

*Department of Organic Chemistry, Pharmaceutical Division, Pennwalt Corporation, Rochester, New York 14623, U.S.A.


The facile opening of the azetidin-2-one ring of the novel spiro[azetidin-2-one-4,2’(or 3,2’)-tricyclo[3.3.1,1 3,7] decanes] 3 and 4 under acidic or alkaline conditions, is described. The reaction led to the preparation of two novel positional isomers, the heretofore difficult to obtain adamantylphenyl-β-alanines 5 and 8.

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Paper | Regular issue | Vol 24, No. 12, 1986, pp. 3451 - 3458
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DOI: 10.3987/R-1986-12-3451
N-Glucosyl-5-amino-4-carbamoyl- and 4-Ethoxycarbonylimidazoles as Potential Precursors of 4-Oxoimdazo[4,5-c]-1,2,6-thiadiazine 2,2-Dioxides

Pilar Goya* and Ana Martinez

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


The syntheses of 1-(tetra-O-acetyl-β-D-glucopyranosyl)-5-amino-4-ethoxy-carbonylimidazole and 1-(tetra-O-acetyl-α and β-D-glucopyranosyl)-5-amino-4-carbamoylimidazole are described. Conversion of the latter to the corresponding 4-cyano derivative is also reported. Related N-substituted 5-amino-4-ethoxycarbonylimidazole derivatives have been cyclized to imidazo[4,5-c]-1,2,6-thiadiazine 2,2-dioxides upon treatment with sulfamoyl chloride.

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Paper | Regular issue | Vol 24, No. 12, 1986, pp. 3459 - 3465
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DOI: 10.3987/R-1986-12-3459
A New Approach to 5-Arylidenethiazolidin-4-ones

Wolf-Dieter Rudorf* and Ralf Schwarz

*Department of Chemistry, Martin-Luther-University Halle-Wittenberg, Halle/Saale, DDR-4050, Germany


Reaction of 3-phenylpropynamides with heterocumulenes in the presence of a base yields 5-arylidenethiazolidin-4-ones by intramolecular nucleophilic addition to the α-carbon of the C≡C triple bond.

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Paper | Regular issue | Vol 24, No. 12, 1986, pp. 3467 - 3471
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DOI: 10.3987/R-1986-12-3467
Solid State Photodimerization Reaction of Some 3-Sytrylisoxazolo[3,4-d]pyridazin-7(6H)-ones

Stefano Chimichi,* Giovanna Ciciani, Vittorio Dal Piaz, Francesco De Sio, Piero Sarti-Fantoni, and Tomas Torroba

*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


The solid state irradiation of the title compounds 4a-b gave two colourless products which were recognized as the corresponding dimers 5a-b. The cyclobutane centrosymmetric structure of the dimers was demonstrated by taking into account the spectroscopic data and the nature of the oxidation products 6a-b.

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Paper | Regular issue | Vol 24, No. 12, 1986, pp. 3473 - 3476
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DOI: 10.3987/R-1986-12-3473
Pyrimidinium N-Dicyanomethylide. Synthesis and Reactivity towards Dimethyl Acetylenedicarboxylate

Antonio de la Hoz,* José Luis G. de Paz, Enrique Díez-Barra, José Elguero, and Carmen Pardo

*Departamento de Química Orgánica, Facultad de Química, Universidad Complutense de Madridas, Ciudad Universitaria, E-28040 Madrid, Spain


The titled compound (1a) has been prepared by reaction of pyrimidine with tetracyanoethyleneoxide (TCNEO). Reaction of 1a with DMAD yielded two regioisomer pyrrolopyrimidines (2a and 3a), via a 1,3-dipolar cycloaddition. Concerning the regioselectivity of the reaction, experimental results are in agreement with theoretical calculations.

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Paper | Regular issue | Vol 24, No. 12, 1986, pp. 3477 - 3482
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DOI: 10.3987/R-1986-12-3477
The Reaction of N-Substituted Dihydropyrimidines with Ketenes

Choji Kashima,* Masao Shimizu, Akira Katoh, and Yoshimori Omote

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


1,4-Dihydro-4,4,6-trimethyl-1-phenylpyrimidine (1) was treated with ketenes prepared from acid chlorides and triethylamine in situ to afford N-acylated ring opened products 2. However, 1 was treated with diphenylketene generated from diphenylacetyl chloride and triethylamine to give the azetidin-2-one derivatives (4).

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Paper | Regular issue | Vol 24, No. 12, 1986, pp. 3483 - 3488
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DOI: 10.3987/R-1986-12-3483
A New Synthesis of Imidazo[5,1-c][1,4]benzoxazines via Their Corresponding Reissert-type Compounds

Herbert Bartsch,* Otto Schwarz, and Gustav Neubauer

*Institute of Pharmaceutical Chemistry, University of Vienna, Währinger Strasse 10, A-1090 Vienna, Austria


A new synthesis of imidazo[5,1-c][1,4]benzoxazines via Reissert-type compounds, obtained from 2-(2-aminophenoxy)-1,1-dimethoxyethane, is described.

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Review | Regular issue | Vol 24, No. 12, 1986, pp. 3489 - 3530
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DOI: 10.3987/R-1986-12-3489
Recent Advances in the Synthesis of Annelated 1,4-Benzodiazepines

Ghulam Mohiuddin, Padala Satyanarayana Reddy, Khalil Ahmed, and Chengalva Venkata Ratnam*

*Department of Chemistry, Osmania University, Hyderabad 500 007, India


This review describes the recent progress in the syntheses of mono- and di-annelated 1,4-benzodiazepines with three, four, five,six and seven-membered rings fused to different positions of 1,4-benzodiazepine nucleus.

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25 data found. 1 - 25 listed