HETEROCYCLES
An International Journal for Reviews and Communications in Heterocyclic ChemistryWeb Edition ISSN: 1881-0942
Published online by The Japan Institute of Heterocyclic Chemistry
Regular Issue
Vol. 26, No. 1, 1987
Published online:
■ Reaction of Amidoximes with α-Chloroacid Chlorides: Novel Synthesis of 1,2,4-Oxadiazin-5-ones
Ahmad Q. Hussein
*Chemistry Department, Faculty of Science, University of Jordan, Amman 11942, Jordan
Abstract
The reaction of amidoximes with α-chloroacid chlorides gives under thermal reaction conditions 5-(1-chloroalky1)-l,2,4-oxadiazoles. In presence of a strong base, the reaction follows a different path leading to the formation of 4H-1,2,4-oxadiazin-5(6H)-ones (4). This latter transformation, involving 0 → N acyl migration, constitutes a new convenient route to compounds 4.
Published online:
■ A New Synthesis of Pyrimido[4,5-b][1,5]benzodiazepin-2-one and -2-thione Derivatives
Kaname Takagi, Hikari Morita, Tomoji Aotsuka, and Yoshihisa Okamoto
*Central Research Laboratories, Zeria Pharmaceutical Co.,, Oshikiri, Konan-machi, Oato-gun, Saitama 360-0111, Japan
Abstract
Derivatives of pyrimido[4,5-b][1,5]benzodiazepin-2- one and -2-thione were synthesized by intramolecular cyclization of N-(3-cyano-1H-1 ,5-benzodiazepin-4-y1)-N’-alkylureas and -N’-phenylthiourea which were obtained by reactions of 4-amino-1H-1,5-benzodiazepine-3-carbonltrile with alkyl isocyanates and phenyl isothiocyanate, respectively.
Published online:
■ Reaction of Benzamiode Oxime Derivatives with Chlorocarbonylsulfenyl Chloride
Etsuko Kawashima, Yuko Ando, Toyozo Takada, and Katsumi Tabei
*Tokyo University of Pharmacy and Life Science, 1432-1 Horinouchi, Hachioji, Tokyo 192-0392, Japan
Abstract
Benzamide oxime derivatives (1) were reacted with chlorocarbonylsulfenyl chloride (2) in the presence of a base as a catalyst to afford 3-aryl-4,5-dihydro-1,2,4 -thiadiazol-5-one (3). 3-aryl-4,5-dihydro-1,2,4-oxadiazol-5-one (4) and di(benzamide) 0,0’-carboxime (5) derivatives in moderate yields. The reaction of N-ethyl-p-toluamide oxime (7) with 2 gave 4-ethyl-4,5-dihydro-3-(p-tolyl)-1,2,4-thiadiazol-5-one (8) and 4-ethyl-4,5-dihydro-3-(p-tolyl)-1,2,4-oxadiazol-5-one (9).
Published online:
■ Reaction of Spiro[piperidine-4,2’-(1’,2’,3’,4’-tetrahydroquinazolin)]-4’-ones with Acetic Anhydride
Masatoshi Yamato, Yasuo Takeuchi and Yuji Ikeda
*Faculty of Pharmaceutical Sciences, Okayama University, 1-1-1 Tsushima-naka, Okayama 700-8530, Japan
Abstract
The tetrahydro derivative (5a) and its aza derivative (5b) of antitumor active amsacrine were prepared. The key synthetic intermediate (3a) was simply prepared by rearrangement of spiro-compound (2a) by heating with acetic anhydride and pyridine. On the other hand, another key intermediate (3b) was obtained only during moderated reaction conditions, and the ring opening products (6b,b’ and 8b,b’) were obtained under the usal conditions.
Published online:
■ A Novel Synthesis of Pyrrolo[2,1,5-de]quinolizinones (Cycl[3.3.2]azinones)
Yasuyoshi Miki,* Hisashi Kinoshita, Toshihiko Yoshimaru, Shoji Takemura, and Masazumi Ikeda
*Faculty of Pharmaceutical Sciences, Kinki University, 3-4-1, Kowakae, Higashi-Osaka 577-8502, Japan
Abstract
3H-Pyrrolo[2,1,5-de]quinolizin-3-ones and a 5H-pyrrolo-[2,1,5-de]quinolizin-5-one were synthesized by the intramolecular aldol condensation of the appropriate 3,5-diacylindolizines.
Published online:
■ Chemistry of α-Cyanothioacetamide
Bahia Y. Riad, Abdallah M. Negm, Sedek E. Abdou, and Hamed A. Daboun
*Department of Chemistry, Faculty of Science, University of Cairo, Giza, Egypt
Abstract
The methods of preparation, chemical properties and utility of a-cyanothioacetamide in the synthesis of sulphur and nitrogen heterocyclic compounds are reviewed.
Published online:
■ Recent Advances in the Synthesis of Phenothiazines
Sayeed Saraf, Fatima Al-Omran, and Balkis Al-Saleh
*Department of Chemistry, Faculty of Science, University of Kuwait, Safat 13060, P.O. Box 5969, Kuwait
Abstract
This paper reviews the most recent methods for the synthesis of phenothiazine derivatives.