Regular Issue

Vol. 27, No. 9, 1988

30 data found. 1 - 30 listed
Communication | Regular issue | Vol 27, No. 9, 1988, pp. 2047 - 2050
Published online:
DOI: 10.3987/COM-88-4552
A Novel Coumaronochromone from the Stems of Euchresta japonica and Its Antibacterial Activity

Mizuo Mizuno,* Koh-ichi Tamura, Toshiyuki Tanaka, and Munekazu Iinuma

*Department of Pharmacognosy, Gifu College of Pharmacy, 6-1 Mitahora-higashi 5-chome, Gifu 502-8585, Japan

Abstract

The structure of a novel highly substituted coumaronochromone, designated as euchretin A, from the stems of Euchresta japonica was established by spectral evidences. Its antibacterial activity is also described.

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Communication | Regular issue | Vol 27, No. 9, 1988, pp. 2051 - 2057
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DOI: 10.3987/COM-88-4572
New Bisindole Alkaloids from Petchia Ceylanica

Atta-ur-Rahman,* Azra Pervin, Anjun Muzaffar, Kuruneruge Tuley Dayanada de Silva,* and Wellage Susil Jayalath Silva

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

Abstract

Two new bisindole alkaloids, ceylanine (1) and ceylanicine (2) have been isolated from Petchia cevlanica and their structures have been established on the basis of spectroscopic techniques.

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Communication | Regular issue | Vol 27, No. 9, 1988, pp. 2059 - 2061
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DOI: 10.3987/COM-88-4595
A Unique Formation of an Isoxazoline-N-oxide from Nitrodibromoacetonitrile and Tetramethylethylene

Joseph H. Boyer* and Thanikavelu Manimaran

*Department of Chemistry, University of New Orleans, New Orleans, LA 70148, U.S.A.

Abstract

Tetramethylethylene and nitrodibromoacetonitrile in dichloromethane at 25°C gave 3-cyano-4,4,5,5-tetramethyl-2-isoxazolin-2-oxide (45%) and 2,3-dibromo-2,3-dimethyl butane (42%).

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Communication | Regular issue | Vol 27, No. 9, 1988, pp. 2063 - 2066
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DOI: 10.3987/COM-88-4608
Rection of Isocynanic Acid and Isocynates with Diketene. Preparation of 2H-1,3-Oxazines, 4-Pyrones, and 2-Pyridones

Shoichiro Ozaki,* Toshio Nagase, and Takazo Kato

*Faculty of Engineering, Ehime University, 3 Bunkyo-cho, Matsuyama, 790-8577 Ehime, Japan

Abstract

Reaction of diketene with isocyanic acid gave the expected product, 2,4-dioxo-6-methyl-3,4-dihydro-2H-1,3-oxazine (2), but with aryl isocyanates gave 3-aryl-2,4-dioxa-6-methyl-3,4-dihydro-2H-l,3-oxazines (3), 3-(arylcarbamoyl)-2,6-dimethyl-4-pyrones (4), and 3-acetyl-1-aryl-4-hydroxy- 6-methyl-2-pyridones (5) depending on the reaction conditions.

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Communication | Regular issue | Vol 27, No. 9, 1988, pp. 2067 - 2070
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DOI: 10.3987/COM-88-4627
Sulphonation of β-Carbolines in Concentrated Sulphuric Acid Solutions

María A. Muñoz, Manuel Balón,* Carmen Carmona, José Hidalgo, and Manuel Lopez Poveda

*Departmento de Química Física, c/Prof. García González s/n, Facultad de Farmacia, Universidad de Sevilla, 41012 Sevilla, Spain

Abstract

Solutions of harmane and N,N-dimethylharmane in concentrated sulphuric acid (16-18M) conducted to the corresponding C-6 sulphonated derivatives.

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Communication | Regular issue | Vol 27, No. 9, 1988, pp. 2071 - 2075
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DOI: 10.3987/COM-88-4628
Synthesis of Pyrrole, Pyrrolidone, Pyrrolo[3,4-c]pyrazole, Pyrrolo[3,2-b]pyridine and Pyrrolo[3,2-b]pyrrole Derivatives

Afaf A. A. Elbannany and Laila I. Ibrahim

*Department of Chemistry, Faculty of Science, Helwan University, Ain-Helwan, Cairo, Egypt

Abstract

A facile and one step route for the synthesis of substituted pyrroie derivatives 5a-g from reaction of ethyl arylidenecyanoacetate (1) with glycine (2) was reported. Also the pyrrolidone derivative ,12 was formed upon reaction of benzylidenemalononitrile (7) with 2 The synthesized 5 has been used as a precursor in the syntheses of pyrrolo[3,4-c]pyrazole 13, pyrrolo[3,2-b]pyridine 15 or its tautomer 16 and pyrrolo[3,2-b]pyrrole derivatives 18.

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Communication | Regular issue | Vol 27, No. 9, 1988, pp. 2077 - 2080
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DOI: 10.3987/COM-88-4636
Syntheses of (1’R)-1’-Methyl-cis-zeatin and Its 9-β-D-Ribofuranoside

Tozo Fujii,* Masashi Ohba, and Miwa Sakari

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

Abstract

The cis isomers III b and IVb of the recently isolated cytokinins (1’R) -1’-methylzeatin (IIIa) and (1”R) -1”-methylzeatin 9-riboside (IVa) have been synthesized from D-alanlne (V) through the intermediates VI, VII, I , V , X, and XI.

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Communication | Regular issue | Vol 27, No. 9, 1988, pp. 2081 - 2085
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DOI: 10.3987/COM-88-4642
Structure of Isorugosin B, and the Orientation of Valoneoyl Group in the Related Monomeric, Dimeric and Trimeric Hydrolyzable Tannins

Tsutomu Hatano, Reiko Kira, Taeko Yasuhara, and Takuo Okuda*

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

Abstract

A new hydrolyzable tannin, named isorugosin B (1), was isolated from Liquidambar formosana, and the structure in which the orientation of valoneoyl group at 0-4 ~ 0-6 of the glucose core is the reverse of that in rugosin B (2) and in rugosin A (3), was determined. The orientation of valoneoyl group in rugosin A (3) was established by the long range 1H-13C correlation nmr spectroscopy. The structures of rugasins D (6), E (7) and G (8), coriariins C (9), D (10), E (11) and F (12), cornusiin A (13), camptothins A (15) and B (16), were fully established on the basis of chemical correlations with 1 or 3.

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Communication | Regular issue | Vol 27, No. 9, 1988, pp. 2087 - 2090
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DOI: 10.3987/COM-88-4644
1,3-Oxazolindid-5-ones, not 1,3-Diazetidinones, are Formed in the Reaction of Tryptophan with Alkyl Isocyanates in the Presence of Acetone

Alf Claesson*

*Research and Development Laboratories, Astra Alab, SE-151 85 Södertälja, Sweden

Abstract

A recent paper in This Journal by Braña et al. (Heterocycles 1987, 26, 95) reports isolation of 2-[(3-alkyl-4,4-dimethyl-2-oxo)-1,3-diazetidinyl]-3-(3-indolylpropionic acids from reactions of tryptophan with alkyl isocyanates in acetone. It appears most likely that these products are instead 1,3-oxazolidin-5-ones.

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Communication | Regular issue | Vol 27, No. 9, 1988, pp. 2091 - 2094
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DOI: 10.3987/COM-88-4646
Synthesis of a New Skeleton, 2,6-Epithio-3-benzazocine

Mikio Hori,* Tadashi Kataoka, Hiroshi Shimizu, Eiji Imai, Noriyuki Iwata, Norihiro Kawamura, and Masayasu Kurono

*Department of Pharmacognosy, Gifu College of Pharmacy, 6-1 Mitahora-higashi 5-chome, Gifu 502-8585, Japan

Abstract

Treatment of isothiochroman 2-oxide derivative (9) with acetic anhydride followed by heating in Dowtherm A (a mixture of biphenyl and diphenyl ether) afforded a novel 2,6-epithio-3-benzazocine derivative (2).

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Communication | Regular issue | Vol 27, No. 9, 1988, pp. 2095 - 2098
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DOI: 10.3987/COM-88-4653
Synthesis of Amphimedine, a New Fused Aromatic Alkaloid from a Pacific Sponge, Amphimedon sp.

Akinori Kubo* and Shinsuke Nakahara

*Meiji Pharmaceutical University, 2-522-1 Noshio, Kiyose, Tokyo 204-8588, Japan

Abstract

Synthesis of the cytotoxic fused pentacyclic aromatic alkaloid, amphimedine 1, is described.

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Communication | Regular issue | Vol 27, No. 9, 1988, pp. 2099 - 2102
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DOI: 10.3987/COM-88-4654
Asymmetric Induction by Chiral Heterocyclic Compounds: Reaction of Chiral N-Methyl-4-phenyl-1,3-oxazolidines with Organometallic Reagents

Hiroshi Takahashi,* Hiroyuki Niwa, and Kimio Higashiyama

*Faculty of Pharmaceutical Sciences, Hoshi University, 2-4-41 Ebara, Shinagawa-ku, Tokyo 142-8501, Japan

Abstract

The reaction of (2S,4R)-2-alkyl-N-methyl-4-phenyl-1,3-oxazolidines (1a-c) with Grignard reagent gave (1R,1’R)-form compounds (2a-c) as the major product. On the contrary, the reaction of 1a-c with organotitanium reagent gave (1S,1’R)-form compounds (3a-c) as the major product. This stereoselectivity is a remarkable characteristic of the reaction of 1,3-oxazolidines with organometallic reagents.

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Communication | Regular issue | Vol 27, No. 9, 1988, pp. 2103 - 2106
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DOI: 10.3987/COM-88-4655
Reinvestigation of the Diels-Alder Reaction of (E)-(R)-4,5-Di-O-isopropylidepent-2-enoates and Cyclopentadiene

Seiichi Takano,* Takumichi Sugihara, Kiyohiro Samizu, and Kunio Ogasawara

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

Abstract

Diels-Alder reaction between (E)-(R)-4,5-di-O-isopropylidenepent-2-enoates and cyclopentadiene under both uncatalyzed and catalyzed conditions has been reinvestigated. Contrary to the preceding reports, no high diastereofacial selection has been observed under both conditions.

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Communication | Regular issue | Vol 27, No. 9, 1988, pp. 2107 - 2110
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DOI: 10.3987/COM-88-4690
Kinetic Resolution of 2-Furylcarbinols Using the Sharpless Oxidation and Its Application to the Synthesis of (5R,6S)-6-Acetoxy-5-hexadecanolide

Tetsuji Kametani,* Masayoshi Tsubuki, Yoko Tatsuzaki, and Toshio Honda

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

Abstract

Kinetic resolution of 2-furylcarbinols employing 10 mol % of Ti(0iPr)4 in the presence of molecular sieves 3A under the Sharpless oxidation condition generally affords corresponding optically actlve 2-furylcarbinols in a range of 80-98% ee. Application of the optically active 1f to the synthesis of (5R,6S)-6-acetoxy-5-hexadecanolide (8), the major component of the oviposition attractant pheromone of the mosquito Culex pipens fatigans, has also been achieved.

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Paper | Regular issue | Vol 27, No. 9, 1988, pp. 2111 - 2118
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DOI: 10.3987/COM-88-4494
Synthesis and Structural Characterization of Octaethyl-17-thiochlorin and Octaethyl-7,17-dithioisobacteriochlorin

Ramesh D. Arasasingham, Alan L. Balch*, and Marilyn M. Olmstead

*Department of Chemistry, University of California, One Shields Avenue, Davis, CA 95616-5295, U.S.A.

Abstract

Conversion of the octaethyl-17-oxochlorin and octaethyl-7,17-dioxoisobacteriochlorin into their thio and dithio analogs using Lawesson’s reagent is reported. Spectroscopic data, along with X-ray crystallographic data for the dithio compound and its dioxo precursor, are reported.

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Paper | Regular issue | Vol 27, No. 9, 1988, pp. 2119 - 2124
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DOI: 10.3987/COM-88-4504
Facile Synthesis of Pyrazole[3,4-b]-pyridines

Abdulla Babaqi, Ali El-Shekeil,* Mohammed Hassan, and Sayed Shiba

*Chemistry Department, Faculty of Science, Sana‘s University, Sana‘s, Yemen

Abstract

The base-catalyzed Michael addition of cyclohexanone, 1,3-diphenyl-2-pyrazolin-5-one, ethyl acetoacetate, and diethyl malonate on 1-aryl-3-(5-chloro-1,3-diphenyl-1H-4-pyrazolyl)-prop-2-en-1-ones (2) in the presence of ammonium acetate at 130°C gave the corresponding pyrazolo [3,4-b] pyridine derivatives (3-6). Structures were confirmed by microanalysis, ir, 1H-nmr, and 13C-nmr.

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Paper | Regular issue | Vol 27, No. 9, 1988, pp. 2125 - 2131
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DOI: 10.3987/COM-88-4535
Synthesis of Substituted Pyridines Using α,β-Unsaturated Nitriles and Active Cyano Compounds

Luis Fuentes,* Juan José Vaquero, Maria Isabel Ardid, Antonio Lerente, and José Luis Soto*

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

Abstract

Several unknown 2-amino-substituted 3,4-dihydropyridines and pyridines are prepared by the reaction of α, β-unsaturated nitriles with active cyano compounds in the presence of a nucleophile reagent.

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Paper | Regular issue | Vol 27, No. 9, 1988, pp. 2133 - 2140
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DOI: 10.3987/COM-88-4539
Biginelli Type Reaction with Tetroses Derivatives

M. Valpuesta Fernández,* F. J. López Herrera, and T. Lupión Cobos

*Departamento de Quimica Organica, Facultad de Ciencias, Universidad de Málaga, Campus de Teations, E-29071 Malaga, Spain

Abstract

The reaction of 2,4-0-ethylidene-D-erythrose and -threose with methyl acetoaoetate and urea, or thiourea, under the conditions of the Biginelli type reaction, gives as principal reaction products C-polyhydroxyalkylpyrimidines derivetives.

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Paper | Regular issue | Vol 27, No. 9, 1988, pp. 2141 - 2152
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DOI: 10.3987/COM-88-4577
Synthesis of New 8-Phenyl[1,2]dithiolo[1,5-b]naphtho[2,1-d][1,2]dithiole-10-SIV, 2,5-Diphenyl-3,4-dihydro-1,6,6a-trithia(6a-SIV)cyclopenta[cd]pentalene and 2,6-Diphenyl-4,5-dihydro-3H-[1,2]dithiolo[4,5,1-hi][1,2]benzodithiole-8-SIV Derivatives

Anotonino Arcoleo,* Giovanni Abbate, Mario Gottuso, Giacomo Fontana, and Gaetano Giammona

*Facolta‘ di Scienze, Dipartimento di Scienze Botaniche - Sezione Fitochimica, Università digli Studi di Palermo, Via Archirafi 20 90123 Palermo, Italy

Abstract

In order to investigate the anti-oxidant properties on lubricant oils, 5,6-dihydro-8-phenyl[1,2]dithiolo[1,5-b]naphtho[2,1-b][1,2]dithiole-10-SIV and a number of phenyl substituted derivatives have been synthesized by cyclization with P2S5 of the corresponding 1,3,5-triketones in toluene. Moreover, some 2,5-diphenyl-3,4-dihydro-1,6,6a-trithia(6a-SIV)cyclopenta[cd]pentalene and 2,6-diphenyl-4,5-dihydro-3H-[1,2]dithiolo[4,5,1-hi][1,2]benzodithiole-8-SIV derivatives have been synthesized by cyclization with P2S5 of the corresponding 2,5-dibenzoylcyclopentanone and 2,6-dibenzoylcyclohexanone derivatives in toluene.

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Paper | Regular issue | Vol 27, No. 9, 1988, pp. 2153 - 2166
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DOI: 10.3987/COM-88-4590
Thermal and Photochemical Oxetane Formation with α-Ketoesters

Jochen Mattay* and Karl Buchkremer

*Institut für Organische Chemie, Rheinisch-Westfälische, Technische Hochsch, Professor-Pirlet-Straße 1, D-52074 Aachen, Germany

Abstract

The thermal and photochemical [2+2]-cycloadditions of ethyl pyruvate, diethyl mesoxalate and biacetyl with 1,1-diethoxyethene, 2,2-diisopropyl-1,3-dioxole and 1,1-dimethoxy-2-methylpropene have been studied. 1,1-Diethouyethene forms oxetanes at room temperature with all carbonyl compounds as well as 1,1-dimethoxy-2-methylpropene and diethyl mesoxalate whereas the other electron-rich olefins generally react only in presence of Lewis-acids as catalysts.These observations indicate the energetic preference of the [1DS+1AS] geometry of the transition state according to Houk’s MO-treatment rather than the [2DS+1AS] geometry for symmetrical olefins. In general the photoreaction is complementary to the therrnal oxetane formation in both the reactivity and the regioselectivity. Only the electron poorest acceptor diethyl mesoxalate did not show any photochemical addition onto these olefins.

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Paper | Regular issue | Vol 27, No. 9, 1988, pp. 2167 - 2174
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DOI: 10.3987/COM-88-4592
Studies on the Constituents of Aconitum Species. VII. On the Components of Aconitum Japonicum Thunb

Hideo Bando, Koji Wada, Takashi Amiya,* Yasuo Fujimoto, and Kimiko Kobayashi

*Hokkaido College of Pharmacy, 7-1 Katsuraoka-cho, Otaru 047-02, Japan

Abstract

Two new diterpenoid alkaloids, subcumine (1) and subcusine (2), were isolated from the roots of Aconitum japonicum Thunb. The structures of these alkaloids were determined on the basis of spectral data, chemical evidence, and X-ray analysis. We also have isolated two known alkaloids, ezochasmaconitine (3) and anisoezochasmaconitine (4).

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Paper | Regular issue | Vol 27, No. 9, 1988, pp. 2175 - 2176
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DOI: 10.3987/COM-88-4605
2,3,6-Triazaphenothiazine

John Barltrop and Terence C. Owen*

*Department of Chemistry, University of South Florida, Tampa, Florida 33620, U.S.A.

Abstract

2,3,6-Triazaphenothiazine has been definitively synthesized and characterrized. A previously reported synthesis appears to be wrong.

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Paper | Regular issue | Vol 27, No. 9, 1988, pp. 2177 - 2183
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DOI: 10.3987/COM-88-4613
An Efficient Synthesis of 5-Aryl(or Alkyl)amino-4-ethoxycarbonyl-2-methylthio-1,3-thiazoles from Dimethyl N-(Ethoxycarbonylmethyl)iminodithiocarbonate and Isothiocyanates

Carlos Alvarez-Ibarra,* Matilde Gil, Paloma Ortiz, and Maria L. Quiroga

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

Abstract

An efficient synthesis of perfunctlonalyzed 1,3-thiazoles 2a-2b with good Yields has been carried out by a cyclocondensation reaction between the α-metallated dimethyl N-(ethoxycarbonylmethyl)iminodithiocarbonate and aryl or alkylisothiocyanates.

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Paper | Regular issue | Vol 27, No. 9, 1988, pp. 2185 - 2196
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DOI: 10.3987/COM-88-4321
New Synthetic Route to Butanolide Lignans by a Ruthenium Complex Catalyzed Hydrogenation of the Corresponding Stobbe‘s Fulgenic Acids

Massimo Bambagiotti-Alberti,* Silvia A. Coran, Franco F. Vinvieri, Nadia Mulinacci, and Giuseppe M. L. Pieraccini

*Dipartimento di Scienze Farmaceutiche, Università di Firenze, Via Gino Capponi 9, I-50121 Firenze, Italy

Abstract

A new two-step total synthesis of butanolide lignans (or dibenzylbutyrolactone lignans) is described, which affords the title compounds in good yield and with a very short work-up time. It involves a ,ruthenium carbonyl hydride complex-catalyzed hydrogenation of the corresponding dibenzylidene succinic acids (fulgenic acids). Since the catalytic hydrogenation (second step) is a total yielding Process, the overall yield determining step is the preparation of the fulgenic acid intermediates by the Stobbe condensation (first step), which has consequently been revised to Improve many details. This simple process moreover allows hexadeuterated butanolide lignans to be readily obtained for isotopic dilution mass spectral measurements. The syntheses of a selection of lignans, namely enterolactone, matairesinol, hinoknin, dimethylmatairesinol and cordigerine, are described to illustrate the whole procedure.

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Paper | Regular issue | Vol 27, No. 9, 1988, pp. 2197 - 2200
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DOI: 10.3987/COM-88-4625
New Acridone Alkaloid and Coumarin from Citrus Plants

Motoharu Ju-ichi,* Hiromi Kaga, Miki Muraguichi, Mami Inoue, Ichiro Kajiura, Mitsuo Omura, and Hiroshi Furukawa

*Faculty of Pharmaceutical Science, Mukogawa-Women‘s University, 11-68 Koushien Kyuban-Cho, Nishinomiya, Hyogo 663-8179, Japan

Abstract

A new acridone alkaloid citramine (1) and a new coumarin osthenon (2) were isolated from the root of the hybrid seedlings of Ogonkan x Hyuganatsu and their structures were elucidated on the basis of spectroscopic data.

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Paper | Regular issue | Vol 27, No. 9, 1988, pp. 2201 - 2211
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DOI: 10.3987/COM-88-4630
Tautomerism in Pyrazino[2,3-c]-1,2,6-thiadiazine 2,2-Dioxides

Pilar Goya, Angela Herrero, Ma. Luisa Jimeno, Carmen Ochoa,* Juan Antonio Páez, Félix Hernández Cano, Concepción Foces-Foces, and Martín Martínez Ripoll

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

Abstract

Tautomerism of pyrazino [2,3-c]-1,2,6-thiadiazine 2,2-dioxides has been studied, in solution, by uv, 13C-, and natural abandance 15N-nmr spectroscopiea and in the solid state by X-ray crystallography. The 1-NH tatutomer is present in solid state and in the majority of solvents. Depending on the 6,7-substituent, the 8-NH tautomer is preferred in water solution. An improved synthesis of 6,7-diaryl substituted pyrazinothiadiazine derivatives is described.

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Paper | Regular issue | Vol 27, No. 9, 1988, pp. 2213 - 2217
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DOI: 10.3987/COM-88-4634
The Effects of Solvent and Temperature on the Orientation of Cycloaddition Reaction of 1,2,3-Triazine Enamines: Its Application to the Synthesis of Alkaloids, Onychine and 6-Methoxyonychine

Teruyo Okatani,* Junko Koyama, Yukio Suzuta, and Kiyoshi Tagahara

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

Abstract

4-Methyl-1,2,3-triazine was treated with several enamines in chloroform to afford 2,5,6-trisubstituted pyridines. In each case, cycloaddition occurs N-3/C-6 of the 1,2,3-triazine nucleus. On the other hand, when high boiling solvent was employed, cycloaddition took place involving the N-3/C-6 cycloadduct and N-1/C-4 cycloadduct. As application of synthetic method, we accomplished the synthesis of alkaloids, onychine and 6-methoxyonychine.

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Paper | Regular issue | Vol 27, No. 9, 1988, pp. 2219 - 2224
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DOI: 10.3987/COM-88-4640
Synthesis of (±)-Roxburghilin and (±)-Epiroxburghilin

Tatsuo Nagasaka,* Hiroto Yamamoto, Akio Sugiyama, and Fumiko Hamaguchi

*School of Pharmacy, School of Pharmacy, 1432-1 Horinouchi, Hachioji, Tokyo 192-0392, Japan

Abstract

The synthesis of (±)-roxburghilin (15) and (±)-epiroxburghilin (16) in six steps from 2-pyrrolidinone is described.

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Review | Regular issue | Vol 27, No. 9, 1988, pp. 2225 - 2249
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DOI: 10.3987/REV-88-392
Synthesis of Condensed Heteroaromatic Compounds Using Palladium-Catalyzed Reaction

Takao Sakamoto, Yoshinori Kondo, and Hiroshi Yamanaka*

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

Abstract

The authors summarize the palladium-catalyzed synthesis of the key intermediates to condensed heteroaromatic rings such as indole, quinoline, isoquinoline, and their azaanalogs and also describe the palladium-catalyzed cyclization to condensed heteroaromatics.

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Review | Regular issue | Vol 27, No. 9, 1988, pp. 2251 - 2288
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DOI: 10.3987/REV-88-395
Synthesis of [2.2.3]Cyclazines, Aza[2.2.3]cyclazines and Their Related Compounds

Yoshinori Tominaga,* Yoshihide Shiroshita, and Akira Hosomi*

*Center of Instrumental Analysis, Nagasaki University, 1-14, Bunkyo-machi, Nagasaki 852-8521, Japan

Abstract

Recent developments in the synthesis of [2.2.3]-cyclazines, benzo[g][2.2.3]cyclazines, benzo[a][2.2.3]cyclazines, dibenzo[a,h][2.2.3]cyclazines, dibenzo[a,g][2.2.3]cyclazines, 1-aza[2.2.3]cyclazines, 5-aza[2.2.3]cyclazines, and 1-azabenzo[h][2.2.3]cyclazines by the [8 + 2] cycloaddition reaction of dimethyl acetylenedicarboxylate (DMAD) with the various type indolizines are summarized by major emphasis that is placed on the results obtained in our own laboratory. The synthesis of indolizines, imidazo[1,2-a]pyridine, and their related compounds which are key intermediates for the synthesis of cyclazines is also described.

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30 data found. 1 - 30 listed