Regular Issue

Vol. 23, No. 1, 1985

104 data found. 1 - 30 listed Next Last
Communication | Regular issue | Vol 23, No. 1, 1985, pp. 1 - 4
Published online:
DOI: 10.3987/R-1985-01-0001
1,3-Dipolar Cycloaddition of 2-Diazopropane to Pyrimido[1,2-b]pyridazun-4-one Derivatives. The Synthesis of Pyrazolo[4,3-d]pyrimido[1,2-b]pyridazin-4(10H)-ones, Derivatives of a Novel Heterocyclic System

Branko Stanovnik,* Breda Boznar, Bozidar Koren, Sasa Petricek, and Miha Tisler

*Department of Chemistry, E. Kardelj University, Murnikova 6, 61000 Ljubljana, Slovenia


Facile regiospecific cycloaddition of 2-diazopropane (2) to the pyrimido[1,2-b]pyridazin-4-ones (1a-d), derivatives of 10Π-electron heteroaromatic bicyclic system, give the pyrazolo[4,3-d]pyrimido[1,2-b]pyridazin-4(10H)-ones (4a-d) in 32-52% yields.

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Communication | Regular issue | Vol 23, No. 1, 1985, pp. 5 - 10
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DOI: 10.3987/R-1985-01-0005
A Synthetic Approach to Noreudesmanoid Phytoalexins

Ajoy K. Banerjee* and María I. Pita Boente

*Centro de Química, Instituto Venezolano de Investigaciones Científicas, I.V.I.C., Apartado 21827, Caracas 1020-A, Venezuela


A stereoselective synthesis of 2β,10β-oxymethylene-4α-methyl-9-oxo-trans-decalin (1) is reported starting from the known dienone (4).

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Communication | Regular issue | Vol 23, No. 1, 1985, pp. 11 - 15
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DOI: 10.3987/R-1985-01-0011
The Structures of Four New Diterpenoid Alkaloids from Delphinium Bonvalotti Franch

Qing Ping Jiang and Wei Liang Sung*

*Institute of Materia Medica, Chinese Academy of MedicalSceince, Nan-wei Road, Beijing 100050, China


Continued investigation of the alkaloids of Delphinium bonvalotii Franch has led to the isolation and structural determination of four new diterpenoid alkaloids, delbotine (1), delboxine (3), delbonine (5) and delbine (6), together with two known bases, deltamine and deltaline. Structures 1 and 3 were confirmed by x-ray analyses. Delboxine (3) and delbine (6) are the first examples of C18-diterpenoid alkaloids bearing C(6)-oxygenated substituent.

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Communication | Regular issue | Vol 23, No. 1, 1985, pp. 17 - 20
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DOI: 10.3987/R-1985-01-0017
Phase Transfer Catalysis in Intramolecular Diels-Alder Reaction of Tertiary Furfurylamines

Dipak Prajapati and Jagir Singh Sandhu*

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


One pot Intramolecular Diels-Alder reaction of tertiary furfurylamines using phase transfer catalysis is reported and cycloadducts are obtained in good yields.

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Communication | Regular issue | Vol 23, No. 1, 1985, pp. 21 - 24
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DOI: 10.3987/R-1985-01-0021
1-Ethyl-3-methylisoguanosine, a Doridosine Derivative

Yong Hae Kim,* Sang Joa Jee, and Harry S. Mosher

*Department of Applied Chemistry, Korea Advanced Institute of Science and Technology, P.O.Box 150 Chong-Yang-ni, Seoul 131, Korea


1-Ethyl-6-imino-3-methyl-2-oxo-9-β-D-ribofuranosylpurine (2, 1-ethyl-3-methyl-isoguanosine) has been synthesized from 5-(methylamino)-1-β-D-ribofuranosylimidazole-4-carbonitrile. This modified purine, by virtue of substituents on both N1 and N3 nitrogens is frozen in the 6-imino form; its uv spectrum is compared to that of analogs which can exist in the tautomeric 6-amino ⇔ 6-imino forms. It is relatively stable to hydrolysis of the 9-ribosyl bond in contrast to other N3-substituted nucleosides.

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Communication | Regular issue | Vol 23, No. 1, 1985, pp. 25 - 27
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DOI: 10.3987/R-1985-01-0025
The Side-chain Acylamination of Alicyclic Nitrones. A New Synthsis of an α-Amino Acid

Dorota A. Abramovitch, Rudolph A. Abramovitch,* and Herman Benecke

*Department of Chemistry, Clemson University, Clemson, SC 29631, U.S.A.


2,4,4-Trimethyl-δ1-pyrroline-1- (4) and 2-n-butyl-4,4-dimethyloxazoline-3-oxide (6) are acylaminated in the presence of base at the α-position of the side-chain at C-2 to give 5 and 10, respectively. Ethanolysis of 10 gives the corresponding α-amino ester (11) in good yield.

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Communication | Regular issue | Vol 23, No. 1, 1985, pp. 29 - 32
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DOI: 10.3987/R-1985-01-0029
Photochemical Reactions of Quinoxalin-2-thiones

Takehiko Nishio* and Yoshimori Omote

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


In contrast with their oxo-analogues (1), quinoxalin-2-thiones (3) undergo photo-induced addition to cyclohexene (4a), methacrylonitrile (4b), and methyl methacrylate (4c) to give 2-substituted quinoxalines (6-14).

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Communication | Regular issue | Vol 23, No. 1, 1985, pp. 33 - 35
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DOI: 10.3987/R-1985-01-0033
Facile Syntheses of Pyrido[2,1-c]-1,4-thiazine Derivatives

Akikazu Kakehi,* Suketaka Ito, Shingo Yonezu, Katsunori Maruta, and Kazuhiro Yuito

*Department of Chemistry and Material Engineering, Faculty of Engineering, Shinshu University, 4-17-1 Wakasato, Nagano 380-8553, Japan


Alkaline treatment of 1-[2-(cyano- or acylmethylthio)vinyl]pyridinium bromides gave smoothly new heterocyclic compounds, 1-cyano- or 1-acyl-1,9a-dihydropyrido[2,1-c]-1,4-thiazine derivatives.

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Communication | Regular issue | Vol 23, No. 1, 1985, pp. 37 - 40
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DOI: 10.3987/R-1985-01-0037
Formation of 2,6-Dialkoxy-3,5-dialkyl-1,4-oxaselenane 1,1-Dichlorides by Reaction of Aliphatic Aldehydes with SeO2 in Alcohols Containing Aqueous HCl

Jan Bergman* and Tarja Laitalainen

*Department of Organic Chemistry, Royal Institute of Technology, SE-100 44 Stockholm, Sweden


A variety of aliphatic aldehydes reacts with SeO2 in alcohols containing aqueous HCl, yielding 2,6-dialkoxy-3,5-dialkyl-1,4-oxaselanane 1,1-dichlorides, albeit unstable, as nicely crystalline compounds. The corresponding C1-stripped compounds are much more stable (distillable) and can be deselenated with degassed Raney nickel to the corresponding 3,4-dialkylfurans.

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Communication | Regular issue | Vol 23, No. 1, 1985, pp. 41 - 44
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DOI: 10.3987/R-1985-01-0041
Stereoselective Formation of a Cyclopentanoid with Three Contiguous Substituents via Inrtamolecular Cycloaddition

Seiichi Takano,* Shigeki Satoh, and Kunio Ogasawara

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


A stereoselective formation of a cyclopentanoid with three contiguous substituents has been demonstrated by using a linear aldehyde and Meldrum’s acid via an intramolecular cycloaddition.

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Communication | Regular issue | Vol 23, No. 1, 1985, pp. 45 - 49
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DOI: 10.3987/R-1985-01-0045
Fluorine-containing Amino Acids and Their Derivatives. 5. Synthesis of Novel Fluorinated Analogues of the Antitumor Agent, Methotrexate

Tadahiko Tsushima,* Kenji Kawada, Osamu Shiratori, and Naomi Uchida

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


Novel methotrexate analogues with γ-fluoro- or α-difluoromethyl-substitued-glutamic acid were synthesized for antitumor screening.

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Communication | Regular issue | Vol 23, No. 1, 1985, pp. 51 - 56
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DOI: 10.3987/R-1985-01-0051
Studies in the Stereospecific Synthesis of Sesbanimide. Approach to Ring C

Nico Willard, Martin J. Wanner, Gerrit-Jan Koomen, and Upendra K. Pandit*

*Laboratory of Organic Chemistry, Institute of Molecular Chemistry, University of Amsterdam, Nieuwe Achtergracht 129, 1018 WS Amsterdam, The Netherlands


Starting from 2-methylpropenol-2 and dimethyl 2,3-dimethylmaleate model approaches for the syntheses of ring C of sesbanimide and 13-oxo-sesbanimide have been developed.

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Communication | Regular issue | Vol 23, No. 1, 1985, pp. 57 - 60
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DOI: 10.3987/R-1985-01-0057
Nucleophilic Addition of Dilithiated Amides to 3-Substituted Pyridines

Ralph Allen Whitney* and John M. Boyle

*Department of Chemistry, Queen’s University, Kingston, Ontario K6L 3N6, Canada


Dilithiated amides (2), derived from N-phenyl or N-methylacetamide and n-BuLi, react with 3-cyanopyridine (1a), 3-(1,3-oxazol-2-in-2-yl)pyridine (1b) or 3-(4,4-dimethyl 1,3-oxazol-2-in-2yl)pyridine (1c) to give dihydropyridines. The major isomer obtained in each case is the 1,6-dihydropyridine (3a-f).

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Communication | Regular issue | Vol 23, No. 1, 1985, pp. 61 - 63
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DOI: 10.3987/R-1985-01-0061
Synthesis of the AB Ring Moiety of Sesbanimide

Masayuki Shibuya*

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


The synthesis of the AB ring moiety of sesbanimide or its enantiomer from D-glucose is described.

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Communication | Regular issue | Vol 23, No. 1, 1985, pp. 65 - 70
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DOI: 10.3987/R-1985-01-0065
Ring Transformation of a 3-Quinoxalinyl-1,5-benzodiazepine into Novel 3-(Benzimidazol-2-ylmethylene)-2-oxo-1,2,3,4-tetrahydroquinoxaline. Convenient Synthesis of Novel 2,3-Fused Quinoxalines

Yoshihisa Kurasawa,* Sayuri Shimabukuro, Yoshihisa Okamoto, and Atsushi Takada

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


Ring transformation of the 3-quinoxalinyl-1,5-benzodiazepine hydrochloride (2) gave novel 3-(benzimidazol-2-yl-methylene)-2-oxo-1,2,3,4-tetrahydroquinoxaline hydrochloride (3a), whose treatment with 5% NaOH afforded the free base (4a). Compounds 3a and 4a were converted into the 2,3-fused quinoxalines (6 and 8) via the oxime (5) and ketone (7), respectively.

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Communication | Regular issue | Vol 23, No. 1, 1985, pp. 71 - 74
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DOI: 10.3987/R-1985-01-0071
Deacylation of 3-Acetyl-4-oxo-6,7-dihydro-12H-indolo[2,3-a]quinolizine

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

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


An unexpected deacylation of 3-acetyl-4-oxo-6,7-dihydro-12H-indolo[2,3-a]qulnolizine (1) on attempted ketalization with ethylene glycol or ethanedithiol and p-toluenesulphonic acid in refluxing benzene to 4-oxo-6,7-dihydro-12H-indolo[2,3-a]quinolizine (3) has been observed.

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Report | Regular issue | Vol 23, No. 1, 1985, pp. 75 - 80
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DOI: 10.3987/R-1985-01-0075
The Synthesis of Polycyclic Structures via Tricarbonyl Cyclohexadietnyl Iron Complexes: Synthesis of 4b-Methyl-9-oxa and 4b-Methyl-B-homo-9-keto-9a-oxaperhydrophenanthrenes

Enrico Mincione,* Paolo Bovicelli, Malcolm Chandler, and Anna Rita Dello Jacono

*Centro CNR per lo Studio della Chimica delle Sostanze Organiche Naturali, Dipartmento di Chimica, Università degli Studi di Roma "La Sapienza", Piazzale Aldo Moro 5, 00185 Roma, Italy


A synthetic route to etherotricyclic structures by elaboration of tricarbonyl cyclohexadienyl iron complexes is described.

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Report | Regular issue | Vol 23, No. 1, 1985, pp. 81 - 92
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DOI: 10.3987/R-1985-01-0081
Studies on Claisen Rearrangement of Bis-propargyl Ethers. Synthesis of Naphthodipyrans, Naphthodifurans and Naphthofuropyrans

Bindumadhavan Venugopalan and Kalpattu Kuppuswamy Balasubramanian*

*Department of Chemistry, Indian Institute of Technology, Madras, 600 036, India


The Claisen Rearrangement of bis-propargyl ethers of naphthalenes yields naphthodipyrans when refluxed in N,N-diethylaniline and naphthodifurans in HMPT in the presence of sodium bicarbonate.

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Report | Regular issue | Vol 23, No. 1, 1985, pp. 93 - 98
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DOI: 10.3987/R-1985-01-0093
Synthesis of Heterocyclic Compounds. XLV. Synthetic Studies Using 2,3-Substituted Propenenitriles: Synthesis of 2-Amino-6-ethylthiopyridines and 3,4-Dihydropyridines

Luis Fuentes,* Juan José Vaquero, Juan Carlos del Castillo, María Isabel Ardid, and José Luis Soto

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


The reactions of malononitrile and arylmethylmalononitriles in alcohols-sodium ethanothiolate with 3-aryl-2-cyanopropenenitriles (1) are studied as a method of synthesis of 2-amino-4-aryl-3,5-dicyano-6-ethylthiopyridines (2) and 2-amino-4-aryl-3-arylmethyl-3,5-dicyano-6-ethylthio-3,4-dihydropyridines (3) respectively. Compounds 3 are isolated as a mixture of diastereoisomers, here designated as α and β. The structure of the 3a(β) isomer (Ar1=Ar2=Ph) has been determined by X-Ray crystallography. Pyridines 4 were obtained by hydrogen cyanide elimination from dihydropyridines 3.

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Report | Regular issue | Vol 23, No. 1, 1985, pp. 99 - 106
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DOI: 10.3987/R-1985-01-0099
Probes for Narcotic Receptor Mediated Phonomena 11. Synthesis of 17-Methyl and 17-Cyclopropylmethyl-3,14-dihydroxy-4,5α-epoxy-6β-fluoromorphinans (Foxy and Cyclofoxy) as Models of Opioid Ligands Suitable for Position Emission Transaxial Tomography

Terrence R. Burke, Jr., Kenner C. Rice,* and Candace B. Pert

*Laboratoryof Chemistry, Medical Chemistry Section, National Arthritis Institute, National Institute of Health, Behesda, Maryland 20892, U.S.A.


Fluorinated derivatives 3,14-dihydroxy-4,5α-epoxy-6β-fluoro-17-methylmorphinan (“fluorooxymorphone”; FOXY, 10) and 17-cyclopropylmethyl-3,14-dihydroxy-4,5α-epoxy-6β-fluoromorphinan (CYCLOFOXY, 18) were prepared based upon the structures of the potent opioid agonist oxymorphone 4 and the antagonist naltrexone 11 respectively. Fluorine was introduced in the final stages of synthesis by a facile nucleophilic displacement with fluoride ion of the 6α-triflate functions in 8 and 16. The synthetic procedures are suitable for the production of the corresponding positron emitting 18F-labeled analogs 18F-FOXY and 18F-CYCLOFOXY, which may be useful for in vivo studies of the opioid receptor system using positron emission trans-axial tomography. In addition, the tritiation of FOXY (10) to high specific activity is described.

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Report | Regular issue | Vol 23, No. 1, 1985, pp. 107 - 110
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DOI: 10.3987/R-1985-01-0107
Oxazolidines and Thiazolidines as Carbon Transfer Agents. Synthesis of Tetrahydro-β-carboline and Isoquinoline Derivatives

Harjit Singh* and Rakesh Sarin

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


Oxazolidines and thiazolidines transfer their C2 units to appropriate nucleophiles and furnish the corresponding tetrahydro-β-carboline and isoquinoline derivatives.

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Report | Regular issue | Vol 23, No. 1, 1985, pp. 111 - 116
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DOI: 10.3987/R-1985-01-0111
Heterocycles. XVI. Methylation of the Cyclic Enamino Ketones

Masayuki Onda,* Yasumasa Sugama, and Reiko Yabuki

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


Methylation of the tetrahydrobenzo[a]quinolizinone 2 and the dihydrobenzo[a]quinolizinone 3 has been examined. The regioselectivity at the nitrogen and oxygen atoms is tremendously affected by the solvents.

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Report | Regular issue | Vol 23, No. 1, 1985, pp. 117 - 120
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DOI: 10.3987/R-1985-01-0117
Reaction of Trialklyl(3-pyridyl)borates with Allylic Bromides in the Presence of Copper(I) Salts. A New Procedure for the Preparation of 3-Allylpyridine Derivatives

Minoru Ishikura, Machiko Kamada, Izumi Oda, and Masanao Terashima*

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


The reaction of lithium trialkyl(3-pyridyl)borates with allylic bromides in the presence of copper (I) salts was found to give 3-allylpyridine derivatives regioselectively.

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Report | Regular issue | Vol 23, No. 1, 1985, pp. 121 - 126
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DOI: 10.3987/R-1985-01-0121
13C NMR Spectra of Cyanidin and Chrysanthemin

Hisato Ikuta, Toshio Fukai, Taro Nomura,* and Jun Uzawa

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


On the 13C nmr spectrum of cyanidin (1), the signal assignments of all the carbon atoms of 1 were carried out by means of selective decoupling and long-range selective 1H decoupling (LSPD) techniques. The 13C nmr spectrum of chrysanthemin (2) isolated from the fruits of Morus alba L. was analyzed with the aid of insensitive nuclear enhanced by population transfer (INEPT) technique as well as of comparison with the 13C nmr spectrum of 1.

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Report | Regular issue | Vol 23, No. 1, 1985, pp. 127 - 132
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DOI: 10.3987/R-1985-01-0127
Synthesis and Properties of Isoselenazolecarboxylic Acids

Francesco Lucchesini, Vincenzo Bertini, and Angela De Munno*

*Dipartimento di Chimica e Chimica Industriale, Università di Pisa, Via Risorgnimento 35, I-56126 Pisa, Italy


Six members of the unknown class of isoselenazolecarboxylic acids are prepared by SeO2 oxidation of 3- and/or 5-methyl substituted isoselenazole derivatives.

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Report | Regular issue | Vol 23, No. 1, 1985, pp. 133 - 137
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DOI: 10.3987/R-1985-01-0133
Reaction of Chloropyrazine N-Oxides with Trimethylaluminum

Akihiro Ohta,* Akira Inoue, Kimie Otshuka, and Tokuhiro Watanabe

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


some 2-chloropyrazine 1- and 4-oxides were submitted to the coupling reaction with trimethylaluminum in the presence of a palladium catalyst. The corresponding 2-methylpyrazine 1- and 4-oxides were obtained in excellent yields.

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Report | Regular issue | Vol 23, No. 1, 1985, pp. 139 - 141
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DOI: 10.3987/R-1985-01-0139
A Convenient One-pot Synthesis of 3-Nitro-2H-chromenes by Ultrasonic Agitation on Basic Alumina

Rajender S. Varma and George W. Kabalka*

*Department of Chemistry, University of Tennessee, Knoxville, Knoxville, TN 37996, U.S.A.


The condensation of o-hydroxybenzaldehydes with β-nitrostyrene derivatives was carried out on basic alumina. Sonic acceleration of this condensation provides a convenient synthesis of 2-phenyl-3-nitro-2H-1-benzopyrans in good yields.

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Report | Regular issue | Vol 23, No. 1, 1985, pp. 143 - 151
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DOI: 10.3987/R-1985-01-0143
The Facile One Pot Synthesis of 6-Substituted 2(1H)-Quinoxalinones

Gozyo Sakata,* Kenzi Makino, and Katsushi Morimoto

*Central Research Institute, Nissan Chemical Industries Ltd., 722-1 Tsuboicho, Funabashi, Chiba 274-8507, Japan


Facile one pot synthesis of 6-substituted 2(1H)-quinoxalinones and these reaction mechanisms are described. The intramolecular cyclization reaction of 4’-substituted 2’-nitroacetoacetanilides in aqueous basic medium and the reduction of 6-substituted 2(1H)-quinoxalinone-4-oxide with sodium borohydride or sodium hydrogensulfite were studied in detail.

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Report | Regular issue | Vol 23, No. 1, 1985, pp. 153 - 157
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DOI: 10.3987/R-1985-01-0153
2,6-Dimethyl-3-cyano-4-thioxothiopyran and Related Molecules from Enaminonitriles and Hydrogen Sulfide by Phase Transfer Catalysis

Jean-Pierre Roggero,* Serge Coen, Bernard Ragonnet, and Catherine Viellescazes

*Faculté des Sciences, Laboratorie de Chimie Organique, 33, rue Louis Pasteur, 84000 Avignon, France


3-Aminocrotonitrile reacts with H2S in the presence of a phase transfer catalyst to yield 2,6-dimethyl-3-cyano-4-thioxothiopyran (liquid-solid catalysis) or the 4-oxo homolog (liquid-liquid catalysis). In the absence of hydrogen sulfide, 2,6-dimethyl-3-cyano-4-pyrone is obtained. The reaction mechanism is discussed.

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Report | Regular issue | Vol 23, No. 1, 1985, pp. 159 - 164
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DOI: 10.3987/R-1985-01-0159
Abnormal Photolysis on N-Benzyl-β-phenethylamine Derivatives Having Bromine and Iodine Atoms

Shigeru Kobayashi,* Masaru Kihara, and Yoshiyuki Miyake

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


Abnormal photolysis of N-benzyl-β-phenethylamines (3a, 3c and 4c) having bromine and iodine atoms provided 4-iodo-5,6,7,8-tetrahydrodibenz[c,e]azocine(1c), and 4-iodo-1,2-methylenedioxy- and 9-iodo-11,12-methylenedioxy-5,6,7,8-tetrahydrodibenz[c,e]azocines (5a and 6a), respectively.

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104 data found. 1 - 30 listed Next Last