Cyclization of [(4- or 5-Substituted-2-benzimidazolyl) thio] acetic Acids. Isolation and Identification of Two Possible Isomers of Substituted Thiazolo [3,2-a] benzimidazol-3 (2H)-one
スポンサーリンク
概要
- 論文の詳細を見る
Cyclizations of [(5-substituted-2-benzimidazolyl) thio] acetic acid (2a-e) to the corresponding thiazolo [3,2-a] benzimidazol-3 (2H)-one (5 and 6) were successfully carried out by heating 2a-e in Dowtherm A or Ac_2O/pyridine, and gave the two possible isomers (5a-e and 6a-e) in a ratio of nearly 1 : 1 in all cases. Separation of 5 and 6 was successfully carried out, and their structures (namely, the direction of cyclization) were suggested on the basis of the NMR spectra. Dowtherm A was more effective than Ac_2O/pyridine, particularly for the cyclization of [(5-nitro-2-benzimidazolyl) thio] acetic acid (2a), which had been reported not to be cyclized with other reagents. Similar cyclization of [(4-methyl-2-benzimidazolyl) thio] acetic acid (2f) preferentially gave 8-methylthiazolo [3,2-a]-benzimidazol-3 (2H)-one (6f).
- 公益社団法人日本薬学会の論文
- 1981-07-25
著者
-
田中 健二郎
School Of Pharmaceutical Science Toho University
-
村上 泰興
School Of Pharmaceutical Science Toho University
-
井野 美知子
School of Pharmaceutical Science, Toho University
-
井野 美知子
School Of Pharmaceutical Science Toho University
関連論文
- Synthetic Studies on Indoles and Related Compounds. XXV. The Friedel-Crafts Acylation of Ethyl 1H-Indole-2-carboxylate. (2)
- Fischer Indolization of Variously ortho-Substituted Phenylhydrazones (Fischer Indolization and Its Related Compounds. XXV)
- Fischer Indolization of Ethyl Pyruvate 2-[2-(Trifluoromethyl)phenyl]-phenylhydrazone and New Insight into the Mechanism of the Goldberg Reaction. (Fischer Indolization and Its Related Compounds. XXVI)
- A NEW SYNTHESIS OF EUPOLAURAMINE FROM A BENZ [f] INDOLE DERIVATIVE
- Synthetic Studies of Indoles and Related Compounds. XXVIII. Intramolecular Vinylation of Pyrrole Derivatives Using Palladium : a New Synthetic Method for Substituted Indoles
- A NEW GENERAL SYNTHETIC ROUTE FOR 1-SUBSITUTED 4-OXYGENATED β-CARBOLINES
- Synthetic Studies on Indoles and Related Compounds. XXVI. The Debenzylation of Protected Indole Nitrogen with Aluminum Chloride. (2)
- Fischer Indolization of Ethyl Pyruvate 2-Bis(2-methoxyphenyl)hydrazone and New Insight into the Mechanism of Fischer Indolization.(Fischer Indolization and Its Related Compounds. XXVII)
- Fischer Indolization and Its Related Compounds. XXIV. Fischer Indolization of Ethyl Pyruvate 2-(2-Methoxyphenyl)phenylhydrazone
- Fischer Indolization and Its Related Compounds. XXIII. Fischer Indolization of Ethyl Pyruvate 2-(2,6-Dimethoxyphenyl)phenylhydrazone
- New Synthetic Method for Dehydrotryptophan Derivatives. Synthetic Studies on Indoles and Related Compounds. XXXIV
- Synthetic Studies on Indoles and Related COmpounds. XXIX. Attempted Syntheses of Benz[f]indoles by Cyclization Reactions
- Abnormal Fischer Indolization and Its Related Compounds. XXII. : Fischer Indolization of Ethyl Pyruvate 2-(2-Chloro- and 2,6-Dichlorophynyl)methylhydrazones
- Reaction of Ethyl Acylindole-2-carboxylates with Thallium Trinitrate (Synthetic Studies on Indoles and Related Compounds. XXXIII)
- Synthetic Studies on Indoles and Related Compounds. XV. : An Unusual Acylation of Ethyl Indole-2-carboxylate in the Friedel-Crafts Acylation
- Synthetic Studies on Indoles and Related Compounds. XII. A Simple General Method for the C-3 Acylation of Ethyl Indole-2-carboxylates
- Determination of the Absolute Configuration of (-)-2-Bromosuccinamic Acid by X-Ray Diffraction Method
- An Efficient Synthesis of 1,1-Disubstituted Hydrazines
- Synthesis of N-Acetylbenzimidazole Derivatives
- Cyclization of [(4- or 5-Substituted-2-benzimidazolyl) thio] acetic Acids. Isolation and Identification of Two Possible Isomers of Substituted Thiazolo [3,2-a] benzimidazol-3 (2H)-one
- Fischer Indolization and Its Related Compounds. XVI. Vilsmeier-Haack Reaction of N-Methyl-1,2,3,4-tetrahydrocarbazole Derivatives
- Fischer Indolization and Its Related Compounds. XV. Vilsmeier-Haack Reaction of 1,2,3,4-Tetrahydrocarbazole Derivatives