HETEROCYCLES

■ Studies on the Reactivity of Isoquinoline and Related Compounds. I. Reaction of Isoquinoline N-Oxide with Diketene

Hiroshi Yamanaka,* Takao Sakamoto, and Takayuki Shiraishi

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

Abstract

The reaction of isoquinoline N-oxide with diketene afforded three products whose structures were assigned 2,6-dimethyl-3-(1-isoquinolyl)-4-pyrone (II), 1-acetonyl-2-acetyl-4-acetoxy-1,2-dihydroisoquinoline (III), and 4-methyl-2-oxo-2H-benzo[a]quinolizine (IV), respectively.

■ Studies on the Reactivity of Isoquinoline and Related Compounds. II. Addition Reaction of Diketene with Isoquinoline and Related Compounds in Acidic Media

Hiroshi Yamanaka,* Takayuki Shiraishi, and Takao Sakamoto

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

Abstract

Addition of diketene in formic, acetic or propionic acid to isoquinoline afforded 1-acetonyl-2-acyl-1,2-dihydroisoquinoline (Va-c) in satisfactory yields. The same reaction was observed to occur in phthalazine and 1,6-naphthyridine.

■ Studies on the Reactivity of Isoquinoline and Related Compounds. III. Addition Reaction of Acetic Anhydride with Isoquinoline and Phthalazine

Hiroshi Yamanaka,* Takayuki Shiraishi, and Takao Sakamoto

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

Abstract

Addition of acetic anhydride to phthalazine and isoquinoline was investigated. The structures of the products were assigned 2-acetyl-1,2-dihydrophthalazine-1-acetic acid and 2-acetyl-1,2-dihydroisoquinoline-1-acetic acid, respectively. In the case of quinoline and quinoxaline this reaction did not occur.

■ The Reaction of Enaminoketones with Benzoyl Isothiocyanate

Otohiko Tsuge* and Akitaka Inaba

*Research Institute of Industrial Science, Faculty of Engineering, Kyushu University, 6-1, Kasuga-koen, Kasuga 816-8580, Japan

Abstract

The reaction of enaminoketone 1a with benzoyl isothiocyanate (7) in benzene afforded 2-thiopyridone derivatives, 8 [1:1 adduct - H₂O and 9 [1:2 adduct - H₂S], and 3-benzamidothiocarbamoyl compound 11 [1:1 adduct]: the relative yields depended upon the reaction conditions. On the other hand, enaminoketone 1b reacted with in benzene to yield the 1-benzoyl-2-thiopyridone 12 [1:2 adduct - (HNCS + H₂O)], while the same reaction in dichloroethane gave the 2-thiopyridone 9b [1:2 adduct - H₂S].

■ Studies on Furan Derivatives. I. A New Preparation of Acetylenes from α-Aryl- or α-2-Furyl-β-2-(5-nitrofuryl)vinylamines

Akira Tanaka,* Toshinao Usui, and Shigetaka Yoshina

*Faculty of Pharmaceutical Sciences, Josai University, 1-1 Keyakidai, Sakado, Saitama 350-0295, Japan

Abstract

β-2-(5-Nitrofuryl)acetylenes (II) were synthesized by the deamination of α-aryl- or α-2-furyl-β-2-(5-nitrofuryl)vinylamines (I).

■ A One Step Synthesis of the Phthalideisoquinoline Alkaloid Cordrastine

Tetsuji Kametani,* Toshio Honda, Hitoshi Inoue, and Keiichiro Fukumoto

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

Abstract

Cordrastine (11a) was synthesised by condensation of 3,4-dihydro-6,7-dimethoxy-2-methylisoquinolinium salt (7) with methyl 6-diazomethyl-2,3-dimethoxybenzoate (8a) derived from 6,7-dimethoxyphthalimidine (20a) . Reaction of 7 with methyl 2-diazomethyl-4,5-dimethoxybenzoate (8b) gave the cordrastine isomer (11b).

■ Photochemical Reactions of Benzotriazoles

Kazuo Tsujimoto,* Mamoru Ohashi, and Teijiro Yonezawa

*The University of Electro-Communications, 1-5-1, Chofugaoka, Chofu, Tokyo 182-0021, Japan

■ Photochemical Syntheses of Heterocyclic Compounds from Hetero-enone System and Ynnone System

Takehiko Nishio,* Hiromu Aoyama, Tadashi Hasegawa, and Yoshimori Omote

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

■ Photochemical Reaction of 2,5-Diphenyl-1,3,4-oxadiazole

Koji Oe, Masashi Tashiro, and Otohiko Tsuge*

*Research Institute of Industrial Science, Faculty of Engineering, Kyushu University, 6-1, Kasuga-koen, Kasuga 816-8580, Japan

■ Photochemistry of o-Nitrobenzaldehyde N-Acylhydrazones Formation of 1-Alkyl-5-nitrophthalazines and Benzotriazinone, and Generation of Benzyne via an Intermediacy of Indazolone

Yoshifumi Maki,* Takashi Furuta, Masayuki Kuzuya, and Mikio Suzuki

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

■ Synthesis of Pyrazolo[3,4-d]pyridazine and Imidazo[4,5-d]pyridazine Derivatives

Kenji Kaji,* Hiromu Nagashima, Yusho Ohta, and Junko Yoshida

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

■ Mechanism of Photocyclization of N-Chloroacetamide Derivatives Having Electron-rich Aromatic Ring

Osamu Yonemitsu,* Yohmei Okuno, Naganori Numao, and Ken-ichi Hirao

*Faculty of Pharmaceutical Sciences, Hokkaido University, Sapporo 060-0812, Japan

■ Photoisomerization of 1,2-Dihydroquinolines: Formation of Indoles and 2,3-Homoindoles

Masazumi Ikeda,* Saeko Matsugashita, Fujio Tabusa, Hiroyuki Ishibashi, and Yasumitsu Tamura

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

■ Photochemical Synthesis of Heterocyclic Systems with Anilides: Oxadative and Non-oxidative Photocyclization Reactions

Yuichi Kanaoka,* Kazuhiko Itoh, and Yasumaru Hatanaka

*Faculty of Pharmaceutical Sciences, Hokkaido University, Sapporo 060-0812, Japan

■ A New Synthesis of 1,2,3,4,6,7,12,12b-Octahydroindole[2,3-a]quinolizine and Oxygenation of Indoloquinolizidine Derivatives

Tohru Hino,* Masako Nakagawa, Toshifumi Asaka, and Yoko Okajima

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

■ Indole-singlet Oxygen Reactions. A Novel Rearrangement of the Peroxidic Intermediates to 2,3-Dihydro-1,4-benzoxazines

Isao Saito,* Mitsuru Imuta, Seichi Matsugo, and Teruo Matsuura

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

■ Reactions of Acyl-aminoquinone Tosylhydrazones. A New Synthesis of Pyrrolo[1,2-a]indoloquinone and Related Compound

Mitsuo Akiba,* Yoshiyuki Kosugi, and Toyozo Takada

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

■ Reaction of Indoles with Succinimido-sulfonium Salts

Kuniyuki Tomita* and Atsusuke Terada

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

■ Syntheses of Fluorinated Heterocyclic Compounds Using Hexafluorobutyne-2

Yoshiro Kobayashi,* Itsumaro Kumadaki, Hiroyuki Mochizuki, Shomi Fujino, and Teruo Kutsuma

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

■ Cycloaddition of 3-Acyl- and 3-Carbethoxy-Δ²-pyrrolin-4,5-dinoes with Olefins

Takehiro Sano,* Yoshie Horiguchi, and Yoshisuke Tsuda

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

■ Addition Reactions of Acid Anhydrides to Isoquinoline and Its Related Compounds

Hiroshi Yamanaka,* Takayuki Shiraishi, and Takao Sakamoto

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

■ Some Reactions of Acetoacetamide Derivatives

Takuo Chiba,* Hiroshi Fukumi, Masaki Noda, and Tetsuzo Kato

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

■ Synthesis and Some Reactions of Mono-alkyl and Aryl Substituted Pyrazines

Akihiro Ohta,* Tokuhiro Watanabe, Yasuo Akita, and Teruo Kurihara

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

■ Heterocycle Synthesis by Diaminocarbene Pb(II) Complex Intermediate

Yoshihiko Ito,* Toshikazu Hirao, and Takeo Saegusa

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

■ Nucleophilic Substitution of Active Methylene Group on Thionyl Chloride and Its Application for the Synthesis of a Few Heterocyclic Compounds

Kitaro Oka* and Shoji Hara

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

■ Syntheses and Reactions of 8-Thiabicyclo[3.2.1]octenone Derivatives

Nobukazu Suto, Tsutomu Miyashi, Toshio Mukai,* and Haruki Tsuruta

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

■ Reactions of Ketenethioacetals Having Pyridinum Salts

Yoshinori Tominaga,* Kazumichi Mizuyama, Yoshinori Miyake, Hiroshi Fujito, Yoshiro Matsuda, and Goro Kobayashi

*Faculty of Pharmaceutical Sciences, Nagasaki University, 1-14, Bunkyo-machi, Nagasaki 852-8521, Japan

■ Reaction of Cyclic Sulfilimines

Masahiro Kise,* Masao Murase, Toshio Tomida, Masahiko Kitano, and Hiromu Murai

*Research Laboratories, Nippon Shinyaku Co., Ltd., 14, Nishinosho-Monguchi-cho, kisshoin, Minami-ku, kyoto, 601-8550, Japan

■ On the Reaction of Dialkyl Acylphosphonate with 2-Methylthiazolium Salts

Akira Takamizawa,* Yoshihiro Matsushita, and Hiroshi Harada

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

■ Synthesis and Reactions of Thiabenzenes

Mikio Hori,* Tadashi Kataoka, Hiroshi Shimizu, Sachio Ohno, Ken’ichi Narita, and Harumi Aoki

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