Regular Issue

Vol. 38, No. 12, 1994

17 data found. 1 - 17 listed
Communication | Regular issue | Vol 38, No. 12, 1994, pp. 2581 - 2584
Published online:
DOI: 10.3987/COM-94-6882
One-Pot Synthesis of Propellane Hetero Analogue from N-Phenyl-substituted 3-Acyl-1,2-dihydrocinnoline-1,2-dicarboximides under Phase-Transfer-catalyzed conditions

Satoko Tanaka, Kazuyoshi Seguchi,* and Akira Sera

*Faculty of Human Life and Environmental Sciences, Mukogawa-Women‘s University, Nishinomiya 663, Japan


Novel propellane hetero analogues were prepared in one-pot from N-phenyl-substituted 3-acyl-1,2-dihydrocinnoline-1,2-dicarboximides under phase-transfer catalyzed.

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Communication | Regular issue | Vol 38, No. 12, 1994, pp. 2585 - 2588
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DOI: 10.3987/COM-94-6896
Synthesis of Annulated Furans with Various 3-Substituents via a Sequential Furannulation/ene Route

Akio Ojida, Akira Abe, and Ken Kanematsu*

*Faculty of Pharmaceutical Sciences, Kyushu University, 3-1-1 Maidashi, Higashi-ku, Fukuoka 812-8582, Japan


Annulated furans with various 3-substituents were synthesized through the one-step synthesis of 3 and its ene reactions with enophiles.

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Communication | Regular issue | Vol 38, No. 12, 1994, pp. 2589 - 2592
Published online:
DOI: 10.3987/COM-94-6908
Synthesis of a New type of Antioxidant possessing Inhibitory Activity against HMG-CoA Reductase

Masakatsu Matsumoto,* Nobuko Watanabe, Eiko Mori, Misao Aoyama, Jun Kusunoki, and Tetsuaki Yamaura

*Department of Chemistry, Faculty of science, Kanagawa University, 2946 Tsuchiya, Hiratsuka 259-1293, Japan


The 6-hydroxychromans (4) and (6), and 5-hydroxy-2,3-dihydrobenzo[b]furans (5) and (7) bearing a 4-hydroxypyran-2-one moiety were synthesized. All the compounds exhibited potent activity against lipid peroxidation. The chroman (4) possessed inhibitory activity against HMG-CoA reductase in addition to the antioxidant character.

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Paper | Regular issue | Vol 38, No. 12, 1994, pp. 2593 - 2603
Published online:
DOI: 10.3987/COM-94-6838
Synthesis of 2,3,5,6-Tetrahydroimidazo[2,1-b]thiazoles

Girts Kaugars,* Scott E. Martin, Stephen J. Nelson, and William Watt

*Animal Health Discovery Research, Upjohn Laboratory, The Upjohn Company, Kalamazoo, MI 49001a, U.S.A.


The reactions of 2-amino-2-thiazoline with alkylating and acylating agents give initial reaction of the endocyclic nitrogen. Acyl groups, however, readily rearrange to the exocyclic nitrogen to give the products usually observed in these reactions. These observations clear up a considerable amount of confusion in the literature and lead to the efficient synthesis of 2,3,5,6-tetrahydroimidazo[2,1-b]thiazoles.

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Paper | Regular issue | Vol 38, No. 12, 1994, pp. 2605 - 2614
Published online:
DOI: 10.3987/COM-94-6844
Intramolecular Cyclization Reaction of Amido-Ureido (or Thioureido)-Acetals

Yong Sup Lee, Choong Sup Kim, and Hokoon Park*

*Organic Chemistry Laboratory, Korea Institute of Science and Technology, P.O. Box 131, Cheongryang, Seoul 130-650, Korea


Intramolecular cyclization reaction of the compound having amide, urea and acetal functional groups was investigated under various conditions. In acidic conditions, the cylclization reaction of N-methyl-N-(2,2-dimethoxyethyl)-N-(alkyl- or phenylcarbamoyl)glycine amide proceeded only to afford imidazolinone derivative via an acyliminium ion intermediate formed by intramolecular amidoalkylation reaction of amide and acetal functional groups. However, the corresponding compounds having thiourea functional group resulted in the formation of iminothiazolidine derivatives as major product and pyrazinone compounds as minor product. In nearly neutral or basic conditions, both of ureido- or thioureidoacetals afforded hydantoin or thiohydantoin derivatives, respectively, in excellent yield.

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Paper | Regular issue | Vol 38, No. 12, 1994, pp. 2615 - 2620
Published online:
DOI: 10.3987/COM-94-6854
Synthesis of 5-Methoxy-2(1H)-quinolinone

María Fernández, Elena de la Cuesta, and Carmen Avendaño*

*Departamento de Química Orgánica y Farmacéutica, Facultad de Farmacia, Universidad Complutense de Madrid, Ciudad Universitaria, 28040 Madrid, Spain


Methylation of 5-hydroxy-2(1H)-quinolinone (1) is studied. The previous protection of the amide group in 1 is proposed as the more convenient method to obtain 5-methoxy-2(1H)-quinolinone (1a).

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Paper | Regular issue | Vol 38, No. 12, 1994, pp. 2621 - 2630
Published online:
DOI: 10.3987/COM-94-6863
Oxidation of 2-Mercaptobenzoheterazoles by Dimethyldioxirane. A New Method for a Synthesis of C-2 Substituted Benzimidazole, Benzoxazole, and Benzothiazole Derivatives

Giuseppe Frachey, Claudia Crestini, Roberta Bernini, Raffaele Saladino,* and Enrico Mincione

*Dipartimento Agrochimico Agrobiologico, Università degli Studi di Viterbo "La Tuscia", Via San Camillo de Lellis, 01100 Viterbo, Italy


New and efficient reactions in which 2-mercaptobenzoheterazoles are selectively converted by dimethyldioxirane, under mild experimental conditions, to several C-2 substituted benzoimidazole, benzoxazole, and benzothiazole derivatives are reported.

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Paper | Regular issue | Vol 38, No. 12, 1994, pp. 2631 - 2654
Published online:
DOI: 10.3987/COM-94-6865
A Facile Epoxidation of 5-Methylene-1,3-dioxane-4,6-diones with Hydrogen Peroxide without Catalyst

Takashi Tsuno,* Kunio Sugiyama, and Hideo Ago

*College of Industrial Technology, Nihon University, 1-2-1, Izumi-cho, Narashino, Chiba 275-8575, Japan


5-Methylene-1,3-dioxane-4,6-diones readily reacted with hydrogen peroxide without any catalyst and any bases to afford the spiro- and poryspirocyclic compounds containing an oxirane ring as crystalline products. Furthermore, the epoxidation of chiral 5-arylidene-1,3-dioxane-4,6-diones with hydrogen peroxide produced the two diastereomers whose purification by silica gel chromatography ensures 100% optical purity.

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Paper | Regular issue | Vol 38, No. 12, 1994, pp. 2655 - 2662
Published online:
DOI: 10.3987/COM-94-6880
Chromenes and Chromanones. Part II. The Birch Reduction of Precocene I and Precocene II

Miroslaw Aniol and Czeslaw Wawrzenczyk*

*Institute of Fundamental Chemistry, Agricultural University , Norwida 25, 50-357 Wroclaw, Poland


The reduction of precocene I (1a), precocene II (1c) and 6-methoxy-2,2-dimethyl-2H-chromene (1b) with sodium or lithium in liquid ammonia was examined. The phenolic compounds and the bicyclic one with partially reduced benzene ring were obtained as the major products from precocene I and 1b, respectively. The demethoxylation during the reduction of precocene II was observed.

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Paper | Regular issue | Vol 38, No. 12, 1994, pp. 2663 - 2676
Published online:
DOI: 10.3987/COM-94-6881
Synthesis and Structural Assignment of Diastereomerically Pure N-Substituted 4-Alkylpyrrolidin-2-ones, Intermediates for the Preparation of 3-Alkylpyrrolidines in Both Enantiomerically Pure Forms

Barbara Cardillo, Roberta Galeazzi, Giovanna Mobbili, Mario Orena,* and Monica Rossetti

*Dipartimento di Scienze dei Materiali e della Terra, Università di Ancona, Via Brecce Bianche, I-60131 Ancona, Italy


By radical cyclisation of N-[(S)-1-phenylethyl]-N-allyliodoacetamides (6a-d), 4-substituted pyrrolidin-2-ones (7a-d) and (8a-d) were prepared as diastereomeric equimolar mixtures which were separated by column chromatography. The preferred conformation of 7a-d and 8a-d was determined by molecular mechanics methods and the configuration of the newly introduced stereogenic center was assigned by 1H nmr data and further confirmed by NOE experiments. Compounds (7a-d) and (8a-d) can be converted into 3-alklpyrrolidines in both enantiomerically pure forms following procedures reported in the literature.

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Paper | Regular issue | Vol 38, No. 12, 1994, pp. 2677 - 2689
Published online:
DOI: 10.3987/COM-01-6886
Synthesis of 6-Formyl Derivatives of 5,8-Dimethoxycarbostyryl

J. Ignacio Ubeda, Carmen Avendaño,* J. Carlos Menéndez, and Mercedes Villacampa

*Departamento de Química Orgánica y Farmacéutica, Facultad de Farmacia, Universidad Complutense de Madrid, Ciudad Universitaria, 28040 Madrid, Spain


An efficient method is described for the preparation of 5,8-dimethoxy-2-oxo-1H-quinoline-6-carbaldehyde. Alternative strategies aimed at the synthesis of 4-methyl analogues are also studied.

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Paper | Regular issue | Vol 38, No. 12, 1994, pp. 2691 - 2694
Published online:
DOI: 10.3987/COM-94-6891
Formation of Organic Semiconductors: Synthesis of Charge Transfer Complexes between TCNQ Radical Anion Salt and Tropylium Ions Fused with Heterocyclic System

Kazuaki Ito and Katsuhiro Saito*

*Faculty of Engineering, Nagoya Institute of Technology, Gokiso-cho, Showa-ku, Nagoya 466-8555, Japan


Tropylium ions fused with heterocyclic systems were synthesized to measure their reduction potentials of - 015 to - 0.37 V vs SCE. Radical anion of TCNQ and these tropylium ions formed charge transfer complexes, which have conductivities of σ = 10-4 - 10-7 Scm-1, suggesting that the belong to semiconductors.

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Paper | Regular issue | Vol 38, No. 12, 1994, pp. 2695 - 8708
Published online:
DOI: 10.3987/COM-94-6911
Synthesis of Phosphono- and Phosphino-substituted Six-membered Heterocycles

Harald G. Krug, Richard Neidlein,* Claus Krieger, and Walter Kramer

*Pharmazeutisch Chemishes Institut, Im Neuenheimer Feld 364, 6900 Heidelberg, Germany


3,6-Dihalopyridazines react with the sodium salts of cyanomethylphosphonic acid dialkyl esters or phenylphosphinic acid ethyl ester to yield phosphono- and phosphino-substituted pyridazines. The constitution of one reaction product is proved by an X-ray crystal structure analysis.

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Paper | Regular issue | Vol 38, No. 12, 1994, pp. 2709 - 2717
Published online:
DOI: 10.3987/COM-94-6906
Sythesis and Stereochemical Studies of New 2-(2-Furyl)cyclanones

Olivier Duval,* Ahmed Rguigue, and Louis M. Gomés

*Laboratoire de Chimie Organique et Thérapeutique, U.F.R de Médecine et Pharmacie, Université d‘Angers, 16, bd. Daviers, 49100 Angers, France


A study was conducted on factors influencing product distributions in the two-step formation of novel 2-(2-furyl)cycloanones using 1H nmr coupling constants values and nOe difference experiments. The 3-(2-furyl)norbornan-2-one and 2-(2-furyl)-5,6-dimethoxy-3-methylidan-1-one unclei were chosen to illustrate pertinent stereochemical criteria which may be exploited in selecting desired derivatives of these species with well defined stereochemistry. These novel adaptable synthons deserved wider recognation as new heterocyclic system promotors.

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Paper | Regular issue | Vol 38, No. 12, 1994, pp. 2719 - 2728
Published online:
DOI: 10.3987/COM-94-6907
Novel and Selective Syntheses of New Analogues of Precocene-2 and Precocene-3 Containing 5-Methyl- or 8-Methyl-substituents

Tibor Tímár,* Péter Sebök, Tibor Eszenyi, and Joseph Cs. Jaszberenyi

*Department of Research, Alkaloida Chemical Co. Ltd., H-4440 Tiszavasvári, POB 1, Hungary


New analogues of precocene-2 and precocene-3 containing 5-methyl- or 8-methyl-substituents have been synthesised in good yields utilising regioselective O-alkylation of 6,7-dihydroxy-2,2,5-trimethyl-4-chromanone and 6,7-dihydroxy-2,2,8-trimethyl-4-chromanone as the key step.

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Paper | Regular issue | Vol 38, No. 12, 1994, pp. 2729 - 2738
Published online:
DOI: 10.3987/COM-94-6910
Convenient Synthesis of a Simple Coumarin from Salicylaldehyde and Wittig Reagent (III): Synthesis of Nitrocoumarins

Takashi Harayama,* Kazumitsu Nakatsuka, Hiromi Nishioka, Kyoko Murakami, Yukiko Ohmori, Yasuo Takeuchi, Hisashi Ishii, and Kazuhiro Kenmotsu

*Faculty of Pharmaceutical Science, Okayama University, 1-1-1 Tsushima-naka, Okayama 700-8530, Japan


Reaction of nitrosalicylaldehydes (1) with carbenthoxymethylenetriphenylphosphorane in Et2NPh, in Ph2O, and in the absence of solvent (neat) at 210-215 °C was investigated. Reaction of 3-nitrosalicylaldehyde (1d) in Et2NPh afforded the benzoxazole (6) and the aminocoumarin (3e) along with the expected coumarin (3d). It was clarified that the origin of carbon-unit introduced for the formation of the benzoxazole ring came from the alkyl group of solvent.

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Paper | Regular issue | Vol 38, No. 12, 1994, pp. 2739 - 2746
Published online:
DOI: 10.3987/COM-94-6914
Synthesis and Activity of New Abscisic Acid Analogues Possessing Hetero Five-membered Ring in their Molecules

Tadao Asami* and Shigeo Yoshida

*The Institute of Physical and Chemical Research, Wako-shi, Saitama 351-0198, Japan


The conjugated dienyl side chain of plant hormone abscisic acid was substituted with five-membered hetero-rings having a carboxyl group on their 2-position. Some of the synthesized compounds showed a remarkable activity similar to ABA in inhibiting cress seed germination and α-amylase induction by gibberellin in half-cut barley seed assays.

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17 data found. 1 - 17 listed