著者

佐伯 清太郎 林 貴昭 浜名 政和

出版者

The Pharmaceutical Society of Japan

雑誌

Chemical and Pharmaceutical Bulletin (ISSN:00092363)

巻号頁・発行日

vol.32, no.6, pp.2154-2159, 1984-06-25 (Released:2008-03-31)

参考文献数

2

被引用文献数

1 6

---

The pseudo-Gomberg reaction of 1-substituted pyrrole derivatives with substituted anilines was examined. Pyrrole derivatives with electron-attracting groups at the 1-position, i.e., ethoxycarbonyl, methanesulfonyl, and benzoyl groups, were found to react smoothly with nitroaniline, chloroaniline and aniline. In each case, 2-arylated pyrrole derivatives were obtained in good or moderate yields.

著者

佐伯 清太郎 近藤 幸子 林 貴昭 浜名 政和

出版者

The Pharmaceutical Society of Japan

雑誌

Chemical and Pharmaceutical Bulletin (ISSN:00092363)

巻号頁・発行日

vol.32, no.5, pp.1780-1789, 1984-05-25 (Released:2008-03-31)

参考文献数

6

被引用文献数

2 6

---

The 1-oxido-4-pyridyl radical generated by the reaction of 4-aminopyridine 1-oxide with amyl nitrite reacted smoothly with aromatic hydrocarbons, including five-membered heterocycles, i.e. thiophene, furan and pyrrole, to give the arylated products when acetic acid was used as the solvent. The relative rates of reaction with the 1-oxido-4-pyridyl radical indicated that this radical is electrophilic, and this finding was supported by a comparison of molecular orbital energy levels. 2-Aminopyridine 1-oxide also undergoes a similar reaction.

著者

舟越 和久 稲田 治明 浜名 政和

出版者

The Pharmaceutical Society of Japan

雑誌

Chemical and Pharmaceutical Bulletin (ISSN:00092363)

巻号頁・発行日

vol.32, no.12, pp.4731-4739, 1984-12-25 (Released:2008-03-31)

参考文献数

14

被引用文献数

3 5

---

Isoquinoline 2-oxide (1) reacts with cyanoacetic acid in the presence of Ac2O to afford various types of 1-substituted isoquinolines (2, 4, 6, and 7) and N-ylides (3 and 5a) depending upon the reaction conditions and processing procedures (Table I). The reaction in Ac2O gives initially α-acetoxycarbonyl-1-isoquinolineacetonitrile (2) and 2-isoquinolinio-acetoxycarbonylcyanomethylide (3), and that in Ac2O-dimethylformamide yields only 3. Products 2 and 3 are readily convertible into α-acetyl-1-isoquinolineacetonitrile (4) and 2-isoquinolinio-acetylcyanomethylide (5a), respectively, by processing involving heating. The reaction in ethanol gives ethyl α-cyano-1-isoquinolineacetate (6) and di (1-isoquinolyl) acetonitrile (7). The reaction of 1 with benzoylacetonitrile affords both the corresponding 1-substituted isoquinoline (10) and N-ylide (11). Reactions with ethyl benzoylacetate and, methyl and ethyl acetoacetates produce 1-substituted isoquinolines (12 and 14a, b) and 4-acetoxyisoquinoline (13), no ylide being formed.

著者

斎藤 裕久 浜名 政和

出版者

公益社団法人 日本薬学会

雑誌

YAKUGAKU ZASSHI (ISSN:00316903)

巻号頁・発行日

vol.99, no.1, pp.23-29, 1979-01-25 (Released:2008-05-30)

参考文献数

14

被引用文献数

1 3

---

Nitration of 1-cyanoisoquinoline 2-oxide (1) with potassium nitrate and sulfuric acid gave 5-and 6-nitro derivatives (2 and 3). The reaction was affected by the concentration of sulfuric acid, and 3 was obtained in small yields as the sole product from the reactions in the 85% acid at 70°. Nitration with fuming nitric acid (d=1.50) led to the formation of 3 in fairly good yields together with small amounts of 8-nitro derivative (7). Further, nitration of isoquinoline 2-oxide (9) with fuming nitric acid was found to give 5-, 6- and 8-nitro derivatives (10, 11 and 12). The orienting effect of the N-oxide function is apparently operative in the formation of 11 and 12.

著者

浜名 政和

出版者

東京大学

巻号頁・発行日

1955

---

博士論文

著者

上田 幾彦 賀来 美夫 佐伯 清太郎 浜名 政和

出版者

日本結晶学会

雑誌

日本結晶学会誌 (ISSN:03694585)

巻号頁・発行日

vol.23, no.Supplement, pp.PA-12, 1981-11-13 (Released:2010-09-30)

著者

永吉 剛 佐伯 清太郎 浜名 政和

出版者

The Pharmaceutical Society of Japan

雑誌

Chemical and Pharmaceutical Bulletin (ISSN:00092363)

巻号頁・発行日

vol.29, no.7, pp.1827-1831, 1981-07-25 (Released:2008-03-31)

参考文献数

27

被引用文献数

4 5

---

Treatment of 1-hydroxy-2-phenylindole (1) with phosphoryl chloride-DMF gave 2-phenylindole-3-carboxaldehyde (2) in 70% yield. The reaction of 1 with quinoline 1-oxide (3) and benzoyl chloride in boiling chloroform produced 1-benzoyloxy-2-phenyl-3-(2-quinolyl) indole (5) and 1-hydroxy-2-phenyl-3-(2-quinolyl) indole (6). In the reaction using tosyl chloride instead of benzoyl chloride, 6 or 2-phenyl-3-(2-quinolyl) indole (8) was formed. These results demonstrate that the enehydroxylamine systems in 1 and 1-benzoyloxy-2-phenylindole (4) can behave as nucleophilic species as a result of enamine-like polarization.

著者

浜名 政和 山崎 企善

出版者

The Pharmaceutical Society of Japan

雑誌

Chemical and Pharmaceutical Bulletin (ISSN:00092363)

巻号頁・発行日

vol.11, no.4, pp.411-414, 1963-04-25 (Released:2008-03-31)

被引用文献数

6 11

---

While quinoline 1-oxide itself is not capable to react with acetyl cyanide, an exothermic reaction occurred in the presence of acetic anhydride, and quinaldonitrile and 2-quinolinepyruvonitrile were obtained. The former was a sole product from the reaction in dioxane or chloroform, whereas the latter was the main product without solvent.

著者

後藤 良宣 山崎 企善 浜名 政和

出版者

The Pharmaceutical Society of Japan

雑誌

Chemical and Pharmaceutical Bulletin (ISSN:00092363)

巻号頁・発行日

vol.19, no.10, pp.2050-2057, 1971-10-25 (Released:2008-03-31)

被引用文献数

15 23

---

Six kinds of 2-aryloxazole N-oxide derivatives were prepared, and their reactions with phosphoryl chloride and acetic anhydride were studied. Methyl group located on the 4-position of 2-aryloxazole N-oxide was easily subjective to nucleophilic attack as an active methyl group in the reaction with phosphoryl chloride or acetic anhydride, whereas 5-methyl group was inert to such an attack.

著者

浜名 政和 舟越 和久 執行 洋陸 口野 嘉幸

出版者

The Pharmaceutical Society of Japan

雑誌

Chemical and Pharmaceutical Bulletin (ISSN:00092363)

巻号頁・発行日

vol.23, no.2, pp.346-350, 1975-02-25 (Released:2008-03-31)

被引用文献数

4 13

---

The 1, 3-dipolar cycloaddition between quinoline N-oxide (I) and methyl propiolate progressed in the presence of acetic anhydride or hydroquinone to afford methyl α-formyl-2-quinolineacetate (IIa). The reaction with ethyl propiolate in the presence of hydroquinone gave the corresponding ethyl ester (IIb). The reaction of I with methacrylonitrile in the presence of hydroquinone produced cyanohydrin of 2-acetonylquinoline (VIII) or 2-acetonylquinoline (IX) and 2-cyanoquinoline (X). Isoquinoline N-oxide (XI) was less reactive and resisted the reaction with propiolates, but reacted with methacrylonitrile in the presence of hydroquinone to give 1-acetonyl-isoquinoline (XII), 1-cyanoisoquinoline (XIII) and isoquinoline.

著者

浜名 政和 山崎 企善

出版者

The Pharmaceutical Society of Japan

雑誌

Chemical and Pharmaceutical Bulletin (ISSN:00092363)

巻号頁・発行日

vol.10, no.1, pp.51-54, 1962-01-25 (Released:2008-03-31)

被引用文献数

7 11

---

Alkaline ferricyanide oxidation of some aromatic N-oxides was examined. Quinoline 1-oxide, lepidine 1-oxide, and isoquinoline 2-oxide were smoothly oxidized to the corresponding N-hydroxy-carbostyrils or-isocarbostyrils. From quinaldine 1-oxide, only a small amount of quinaldinic acid 1-oxide was obtained. In contrast, pyridine and nicotinic acid 1-oxide were not affected by this oxidation procedure.

著者

浜名 政和 山崎 企善

出版者

The Pharmaceutical Society of Japan

雑誌

Chemical and Pharmaceutical Bulletin (ISSN:00092363)

巻号頁・発行日

vol.11, no.4, pp.415-421, 1963-04-25 (Released:2008-03-31)

被引用文献数

21 31

---

Quinoline 1-oxides were found to react smoothly with compounds containing reactive hydrogens in the presence of acetic anhydride, producing the corresponding 2-substituted quinolines. The yields were generally good to excellent in the reactions of ethyl cyanoacetate, 1, 3-indandione, diethyl malonate, diethyl nitromalonate, ethyl nitroacetate (e. g. ethyl α-cyano-2-quinolineacetate in 88% yield), but acetone, acetophenone or phenylacetonitrile could not enter into the reaction. The reaction of quinoline 1-oxide using benzoyl chloride instead of acetic anhydride and those of pyridine 1-oxides in the presence of acetic anhydride proceeded similarly but in much lower yields.

著者

佐伯 清太郎 山下 絢子 盛中 泰洋 浜名 政和

出版者

The Pharmaceutical Society of Japan

雑誌

Chemical and Pharmaceutical Bulletin (ISSN:00092363)

巻号頁・発行日

vol.25, no.1, pp.79-86, 1977-01-25 (Released:2008-03-31)

被引用文献数

1 2

---

1, 1-Ethylenedioxy-9-(2-pyridyl) quinolizidine (1) was converted to N-ethoxycarbonylpyridinium salt (3) via monohydrobromide (2) by successive treatment with ammonium bromide and ethyl bromoacetate. The reaction of 3 with hydrochloric acid was markedly affected with the concentration of the acid. Thus, when 3 was heated with 15-20% hydrochloric acid, ring closure took place accompanied by hydrolysis of the ketal and ester groups and also decarboxylation to give 17-hydroxy compound (4). Heating with triethylamine gave dehydrated pyridinium salt (5) which was reduced with sodium borohydride and then catalytically to dl-allomatridine (6). On the other hand, heating 3 with 5-10% hydrochloric acid gave a carboxylic acid (9) which was also transformed into 6 through an ester (10) and a ring closure product (11) as shown in Chart 2. The action of 30% acid on 3 followed by the similar treatments afforded 1-hydroxy-9-(2-pyridyl) quinolizidine (7). Transformation of 1 to 17-hydroxyallomatridine (8) was further achieved successively by hydrolysis to 1-oxo compound (12), formation of its cyanohydrin (13) and hydrogenation over Raney nickel.