Regular Issue

Vol. 9, No. 2, 1978

11 data found. 1 - 11 listed
Communication | Regular issue | Vol 9, No. 2, 1978, pp. 139 - 144
Published online:
DOI: 10.3987/R-1978-02-0139
Two New Sesquiterpenoids from Chloranthus glaber Makino

Masaaki Uchida, Genjiro Kusano, Yoshikazu Kondo, Shigeo Nozoe,* and Tsunematsu Takemoto

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


Two new sesquiterpenes, chloranthalactone A (I) and B (II) were isolated from Chloranthus glaber Makino and characterized.

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Communication | Regular issue | Vol 9, No. 2, 1978, pp. 145 - 152
Published online:
DOI: 10.3987/R-1978-02-0145
The Methylene Signature of Reduced Isoquinolines: A PMR Structural Correlation

Jerome L. Moniot and Maurice Shamma*

*Department of Chemistry, The Pennsylvania State University, York Campus, P1031 Edgecomb Avenue, York, Pennsylvania 17403, U.S.A.


The ring B methylene proton signals in the pmr spectra of reduced isoquinolines appear as symmetrical triplets when nitrogen inversion is precluded, and as complex multiplets when the nitrogen atom can undergo inversion. The chemical shifts for the ring B protons on the carbon adjacent to nitrogen are dependent on the state of that nitrogen atom, and are in the following order of increasing δ values: Amines

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Communication | Regular issue | Vol 9, No. 2, 1978, pp. 153 - 160
Published online:
DOI: 10.3987/R-1978-02-0153
Cycloaddition of 2-Phenyl-3-ethoxycarbonyl-Δ2-pyrroline-4,5-dione to Cyclopentadiene

Yoshisuke Tsuda,* Miyuki Kaneda, Yoshitaka Itatani, Takehiro Sano, Yoshie Horiguchi, and Yoichi Iitaka

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


Cycloaddition of 2-phenyl-3-ethoxycarbonyl-Δ2-pyrroline-4,5-dione to cyclopentadiene in either photochemical or thermal condition gave three products: the dihydropyridone (A), the cyclobutane (B), and the bicycloheptane (C), the structures of which were established by spectroscopic means and by X-ray analyses of their bromo-derivatives. A possible mechanitic rationalization would involve [2a+2s] cycloaddition governed by donor-acceptor interaction followed by cleavage and recombination of a trans-fused cyclobutane.

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Communication | Regular issue | Vol 9, No. 2, 1978, pp. 161 - 168
Published online:
DOI: 10.3987/R-1978-02-0161
A New Route to 3,4-Dihydro-2-pyridones from a Dioxopyrroline Derivative

Takehiro Sano,* Yoshie Horiguchi, Yoshisuke Tsuda,* and Yoshitaka Itatani

*Showa Pharmaceutical University, 3-3165, Higashi-tamagawagakuen, Machida, Tokyo 194-8543, Japan


In photocycloaddition of 2-phenyl-3-ethoxycarbonyl-Δ2-pyrroline-4,5-dione to olefins, the formation of dihydropyridones were observed although the yields were variable depending on the structure of olefins.

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Communication | Regular issue | Vol 9, No. 2, 1978, pp. 169 - 173
Published online:
DOI: 10.3987/R-1978-02-0169
Reaction of 1-Phenyl-4-hydrazino-4,5-dihydro-6H-furo[2,3-d][1]benzazepine-5-carboxylic Acid Hydrazide with Aromatic Aldehydes

Kazuo Ito, Kenichi Yakushijin, and Shigetaka Yoshina*

*Faculty of Pharmacy, Meijo University, 150 Yagoto, Tempaku-ku, Nagoya, Aichi 468-8503, Japan


l-Phenyl-4-hydrazino-4,5-dihydro-6H-furo[2,3-d][1]benzazepine-5-carboxylic acid hydrazide (2) reacts with aromatic aldehydes in ethanol to give saturated monoarylylidene compounds (3a-c) and unsaturated monoarylylidene compounds (5a-c), respectively.

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Communication | Regular issue | Vol 9, No. 2, 1978, pp. 175 - 183
Published online:
DOI: 10.3987/R-1978-02-0175
Synthesis of the Antibiotic, (±)-Pyridindolol

Geng Wu, Etsuji Yamanaka, and James M. Cook*

*Department of Chemistry, University of Wisconsin-Milwaukee, Milwaukee, Wisconsin 53201, U.S.A.


Pictet-Spengler condensation of tryptophan methyl ester 7 with glyceraldehyde acetonide 8 in refluxing benzene provided the 1,2,3,4-tetrahydro β-carboline 9 in good yield. The β-carboline was then converted in three steps to the β-galactosidase inhibitor, pyridindolol 1.

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Communication | Regular issue | Vol 9, No. 2, 1978, pp. 185 - 192
Published online:
DOI: 10.3987/R-1978-02-0185
1,3-Oxazines and Related Compounds. III. Ring Contraction Reaction of 1,3-Oxazin-4-one Derivatives into 1,2,4-Oxadiazoles and Isoxazoles

Yutaka Yamamoto* and Yutaka Azuma

*Faculty of Pharmaceutical Sciences, Tohoku Pharmaceutical University, 4-4-1 Komatsushima, Aoba-ku, Sendai 981-8558, Japan


Reaction of 2-phenyl-, 2-(2-pyridyl)-, 2-(3-pyridyl)- and 2-(2-quinolyl)-6-methyl-4H-1,3-oxazin-4-one (1a-d) with hydroxylamine hydrochloride in the presence of sodium acetate or sodium alkoxide led to a formation of the corresponding 1,2,4-oxadiazoles 4a-d in 72%, 65%, 80%, and 71% yield, respectively.
On the other hand, treatment of 1a-d with hydroxylamine hydrochloride in 95% ethanol gave rise to the corresponding isoxazoles 7a-d.
Analogously, the 2,3-dihydro-1,3-oxazine 1e underwent the ring contraction into the 1,2,4-oxadiazole 4e and isoxazole 7e in 32% and 56% yield, respectively.

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Communication | Regular issue | Vol 9, No. 2, 1978, pp. 193 - 195
Published online:
DOI: 10.3987/R-1978-02-0193
Synthesis of the Alkaloid Haplobucharine

Pietro Venturella* and Aurora Bellino

*Dipartimento di Chimica Organica, Università digli Studi di Palermo, Via Archirafi 20 90123 Palermo, Italy


A simple synthesis of haplobucharine [I], an alkaloid isolated from Haplophillum bucharicum was described.

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Report | Regular issue | Vol 9, No. 2, 1978, pp. 197 - 200
Published online:
DOI: 10.3987/R-1978-02-0197
Reaction of 6-Amino-1,3-Dimethyluracils with Ethoxymethylenemalononitrile

Katsuhiko Nagahara* and Atsushi Takada

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


Treatment of 6-amino-1,3-dimethyluracil with ethoxymethylenemalononitrile (EMMN) afforded 1,3,7,9-tetramethylpyrido[2,3-d:6,5-d’]dipyrimidine-2,4,6,8-(1H,3H,7H,9H)-tetrone and 7-amino-6-cyano-1,3-dimethylpyrido[2,3-d]pyrimidine-2,4(1H,3H)-dione. On the other hand, reaction of 6-hydrazino-1,3-dimethyluracil with EMMN gave 6-(3-amino-4-cyanopyrazol-2-yl)-1,3-dimethyluracil.

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Report | Regular issue | Vol 9, No. 2, 1978, pp. 201 - 206
Published online:
DOI: 10.3987/R-1978-02-0201
Studies on ths Synthesis of Bisindole Alkaloid. XII. Derivatives of Vincristine

James P. Kutney,* John Balsevich, Toshio Honda, Ping-Huang Liao, Herman P. M. Thiellier, and Brian R. Worth

*Department of Chemistry, University of British Columbia, 2036 Main Mall, Vancouver, B.C. V6T 1Z1, Canada


Specific Jones’oxidation of 3’,4’-dehydrovinblastine, leurosine, 19’-oxoleurosine, 6,7-dihydra-4’-deoxyleurosidine and 3’,4’-dehydro-3-desvarbomethoxy-3-N-methylcarboxamldovinblastine provided the corresponding 22-oxo-derivatives of the vincristine series. Further oxidation of 22-oxoleurosine, with iodine/sodium bicarbonate, gave the 19’-oxo-bisindole.

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Report | Regular issue | Vol 9, No. 2, 1978, pp. 207 - 210
Published online:
DOI: 10.3987/R-1978-02-0207
A Base-catalyzed Oxygenation of the β-Apolignan: A Biogenetic Model

Takefumi Momose* and Ken-ichi Kanai

*Faculty of Pharmaceutical Sciences, Osaka University, 1-6 Yamadaoka, Toyonaka, Osaka 560-0043, Japan


A biogenetic-type transformation of the β-apolignan (I) into naphthalide lignans (II and III) by a base-catalyzed oxygenation is described.

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11 data found. 1 - 11 listed