HETEROCYCLES

■ Polymethoxylated Ioquinokines as Potential Antimitotic Agents

Maria Iorio, Arnold Brossi,* and Colin F. Chignell

*Laboratory of Chemical Diseases, National Institute of Diabetes and Digestive and Kidney, National Institute of Health, Bethesda, MD 20892, U.S.A.

Abstract

Several polymethoxylated isoquinolines related to the alkaloids sendaverine and cryptostyline III have been prepared from mescaline. Using colchicine as a standard none of these compounds did show any binding affinity to the rat brain microtubule protein.

■ A New, Facile Synthesis of 10-Arylisoalloxazines

Fumio Yoneda,* Kazuo Shinozuka, Yoshiharu Sakuma, and Yoshihiro Nitta

*Faculty of Pharmaceutical Sciences, Kumamoto University, 5-1 Oe-hon-machi, Kumamoto 862-0973, Japan

Abstract

The condensation of 6-arylaminouracils with nitrosobenzenes in acetic anhydride gave the corresponding 10-arylisoalloxazines.

■ Synthesis of Pyrimido[4,5-c]pyridazine Derivatives

Sadao Nishigaki, Misuzu Ichiba, Junko Sato, Keitaro Senga,* Mitsuko Noguchi, and Fumio Yoneda

*Pharmaceutical Institute, School of Medicine, Keio University, Shinanomachi 35, Shinjuku, Tokyo 160-0016, Japan

Abstract

Treatment of 6-hydrazino-l,3-dimethyluracil (I) with phenacyl bromides afforded the corresponding 3-aryl-6,8-dimethylpyrimido[4,5-c]pyridazine-5,7(1H,2H,6H,8H)-diones (IIa-e) and 3-aryl-6,8-dimethylpyrimido[4,5-c]pyridazine-5,7(6H,8H)-diones (IIIa-e) , respectively. The oxidation of II with diethyl azodicarboxylate provided III. The reaction of 6-benzylidene-l,3-dimethyluracils with dimethylformamide dimethylacetal also gave III.

■ Conformational Equilibrium in cis-Octahydrocarbostyrils

Takefumi Momose,* Tastuo Miyata, and Takeshi Imanishi

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

Abstract

The proton magnetic resonance (¹H-NMR) studies on N-substituted cis-octahydrocarbostyrils have revealed a preference of the conformer (2_eq) for the substituent methyl or benzyl and of the conformer (2_ax) for the N-hydrogen compound. The positions of conformational equilibrium [2_eq ⇔ 2_ax] in several other cis-octahydrocarbostyrils are also described.

■ Some Diazaspiranes from the Reaction of Ketones with Ethylenediamine and 1,3-Diaminopropane

John W. ApSimon,* R. Wayne Thompson, John C. S. Wong, and William G. Craig

*Department of Chemistry, Carlton University, 1125 Colonel By Drive, Ottawa Ont. KaS 5B6, Canada

Abstract

The reaction of a variety of ketones with ethylenediamine and 1,3-diaminopropane has been found to provide the expected 2,2 substituted diazaspiranes.

■ New Synthesis of Pyrimido[5,4-e]-as-triazines by the Reaction of 6-Hydrazino-1,3-dimethyl-5-nitrosouracil with Benzylidenetriphenylphosphoranes

Keitaro Senga,* Misuzu Ichiba, Yukako Kanamori, and Sadao Nishigaki

*Pharmaceutical Institute, School of Medicine, Keio University, Shinanomachi 35, Shinjuku, Tokyo 160-0016, Japan

Abstract

Treatment of 6-hydrazino-l,3-dimethyl-5-nitrosouracil with benzylidenetriphenylphosphoranes gave the corresponding 3-arylfervenulins (3-aryl-6,8-dimethylpyrimido[5,4-e]-as-triazine-5,7(6H,8H)-diones).

■ Ring-Modifying Reactions of Pyrimidines Containing a Quaternary Nitrogen

Henk C. van der Plas*

*Laboratory of Organic Chemistry, Agricultural University, De Dreijen 5, 6703 BC Wageningen, The Netherlands

■ Synthesis and Reaction of Benzo- and Dibenzo-tropone Oxides

Takahiro Tezuka,* Miyoshi Shinba, and Yasushi Nagai

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

■ Biomimetic Asymmetric Synthesis of 3-Substituted Dihydroisocarbostril Derivatives

Toshio Wakabayashi* and Kenzo Watanabe

*Teijin Institute, Asahigaoka 4-3-2, Hino, Tokyo 191, Japan

■ Oxygenation of 2,3-Diphenylindoles

Tohru Hino,* Masako Nakagawa, Noriko Ohyoshi, Shiro Kato, Mutsumi Takano, and Akiko Hirose

*Faculty of Pharmaceutical Sciences, Chiba University, 1-33 Yayoi-cho, Inage-ku, Chiba 263-8522, Japan

■ New Indole Trimer

Hisashi Ishii,* Keiko Murakami, and Yasuoki Murakami

*Faculty of Pharmaceutical Sciences, Chiba University, 1-33 Yayoi-cho, Inage-ku, Chiba 263-8522, Japan

■ Synthesis of Heterocycles via Intramolecular Cyclizations of N-Substituted Enamino Ketones

Hideo Ida,* Sakae Aoyagi, Tatsutoshi Takarai, Yoshifumi Yuasa, and Chihiro Kibayashi

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

■ A Novel Synthesis of Substituted Indoles by Photochemical Ring-contraction of Benz[d]-3,1-oxazepines

Chikara Kaneko,* Reiko Kitamura, Atsushi Yamamoto, Harue Fujii, and Masanori Somei

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

■ Heterocycle Synthesis Using o-Tolyl Isocyanide. Syntheses of Indole and Dihydroxazepine Derivatives

Yoshihiko Ito,* Kazuhiro Kobayashi, and Takeo Saegusa

*Department of Synthetic Chemistry, Faculty of Pharmaceutical Sciences, Kyoto University, Yoshida, Sakyou-ku, Kyoto 606-8501, Japan

■ Meldrum’s Acid in Organic Synthesis. New Syntheses of Indolepropionic Esters and β-Ketoesters

Yuji Oikawa* and Osamu Yonemitsu

*Faculty of Pharmaceutical Sciences, Hokkaido University, Kita 12 Nishi 6, Kita-ku, Sapporo, Hokkaido 060-0812, Japan

■ Synthetic Approaches to Velbanamine, Vindoline, Vincamine, and Emetine

Seiichi Takano,* Susumi Hatakeyama, Shinichi Yamada, Hideyuki Kanno, Makoto Sasaki, Masaaki Sato, Kozo Shishido, and Kunio Ogasawara

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

■ Structure and Relative Stereochemistry of Alangimarckine: A Total Synthesis of (±)-Alangimarckine

Tozo Fujii,* Shigeyuki Yoshifuji, and Hiroshi Kogen

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

■ A New Stereoselective Synthesis of Emetine and Related Alkaloids

Tetsuji Kametani,* Masataka Ihara, Yukio Suzuki, Hirofumi Terasawa, and Keiichiro Fukumoto

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

■ Synthesis of Mimosamycin (2,6-Dimethyl-7-methoxy-3,5,8-isoquinolinetrione)

Hiroshi Fukumi,* Hideshi Kurihara, and Hiroshi Mishima

*Medicinal Chemistry Research Laboratories, Sankyo Co., Ltd., 1-2-58 Hiromachi, Shinagawa-ku, Tokyo 140-8710, Japan

■ A New Synthesis of the Heterocycles Related to Ipecac and Yohimbe Alkaloids

Ichiya Ninomiya,* Yukio Tada, Toshiko Kiguchi, and Okiko Yamamoto

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

■ The Synthesis of Heterocyclic Compounds by Use of Organometallic Complex. The Synthesis of Oxindole and Isoquinoline Alkaloids

Miwako Mori,* Katsumi Chiba, Satsuko Kudo, Toshihito Ikeda, Yasuko Hashimoto, and Yoshio Ban

*Faculty of Pharmaceutical Sciences, Hokkaido University, Kita 12 Nishi 6, Kita-ku, Sapporo, Hokkaido 060-0812, Japan

■ Synthesis of Natural Prosducts via Isoxazolidines and Isoxazolines

Takenori Kusumi,* Satoru Takahashi, Shinichiro Suzuki, Kaoru Harada, and Hiroshi Kakisawa

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

■ Synthesis of Urethane Derivatives by Reactions of α-Bromoacylophenones or Epichlorohydrin with Carbon Dioxide and Aliphatic Amines and Reactions of the Obtained Urethane Derivatives

Takashi Toda* and Takashi Asano

*Department of Chemistry, Faculty of Science, Tohoku University, Aoba-ku, Ssendai 980-8578, Japan

■ Syntheses of 4-(C-Glycosyl)isoxazoline N-Oxides and Related Substances

Eisuke Kaji,* Hiromi Ichikawa, and Shonosuke Zen

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

■ Synthesis and Spectral Properties of Bis- and Tris(metalloporphyrins)

Kunihiro Ichimura* and Sakayuki Takeuchi

*Research Institute for Polymer and Textiles, Sawatari 4, Kanagawa-ku, Yokohama, Japan

■ One-Step Porphyrin Synthesis by Use of Schiff Bases

Iwao Tabushi,* Ko-ichi Sakai, and Kazuo Yamamura

*Department of Synthetic Chemistry, Faculty of Pharmaceutical Sciences, Kyoto University, Yoshida, Sakyou-ku, Kyoto 606-8501, Japan

■ Synthesis and Reactions of 1,3,4,6-Tetrakis(trifluoromethyl-2,5-diphosphatricyclic[3.1.0.0^2,6]]hexene-3

Yoshiro Kobayashi,* Shomi Fujino, Hiroshi Hamana, Itsumaro Kumadaki and Yuji Hanzawa

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

■ The Reactions and Optical Resolutions of 1-Arly-4,6-dimethyl-2(1H)-pyrimidinones

Choji Kashima,* Akira Katoh, Takehiko Nishio, Tatsuo Otsuka, and Yoshimori Omote

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

■ New Synthesis of Fused Pyrimidines by the Use of 6-Methyluracil Derivatives

Shigeo Senda,* Kosaku Hirota, Tatsuji Asao, and Yoshihiro Yamada

*Gifu Pharmaceutical University, 6-1 Mitahora-higashi 5-chome, Gifu 502-8585, Japan

■ The Synthesis of Pyrazolo[3,4-d]pyrimidine and Pyrimido[4,5-e][1,3,4]thiadiazine Derivatives from 6-Hydrazinouracils

Takehiko Naka* and Yoshiyasu Furukawa

*Takeda Chemical Industries, Ltd., 17-85 Jusohonmachi 2-chome, Yodogawa-ku, Osaka 532-8686, Japan