Efficient TCT-catalyzed Synthesis of 1,5-Benzodiazepine Derivatives under Mild Conditions.docVIP

Molecules 2008, 13, 2313-2325; DOI: 10.3390/moleculeOPEN ACCESS molecules ISSN 1420-3049 /molecules Article Efficient TCT-catalyzed Synthesis of 1,5-Benzodiazepine Derivatives under Mild Conditions Chun-Wei Kuo, Chun-Chao Wang, Veerababurao Kavala and Ching-Fa Yao * Department of Chemistry, National Taiwan Normal University, 88, Section 4, Tingchow Road, Taipei 116, Taiwan, ROC * Author to whom correspondence should be addressed; E-mail: cheyaocf@.tw; Tel.: +886-2-2930-9092; Fax: +886-2-2932-4249. Received: 22 August 2008; in revised form: 10 September 2008 / Accepted: 10 September 2008 / Published: 25 September 2008 Abstract: 2,4,6-Trichloro-1,3,5-triazine (TCT) efficiently catalyzed the condensation reactions between 1,2-diamines and various enolizable ketones to afford 1,5-benzodiazepines in good to excellent yields. Simple and mild reaction conditions, the use of a cheap catalyst and easy workup and isolation are notable features of this method. Keywords: Benzodiazepines, 2,4,6-trichloro-1,3,5-triazine, enolizable ketones, o-phenylenediamines. Introduction Benzodiazepines and its derivatives constitute an important class of heterocyclic compounds which possess a wide range of therapeutic and pharmacological properties. Derivatives of benzodiazepines are widely used as anticonvulsant, antianxiety, analgesic, sedative, antidepressive, and hypnotic agents [1-2]. In the last decade, the area of biological interest of 1,5-benzodiazepines has been extended to several diseases such as cancer, viral infection and cardiovascular disorders [3-4]. In addition, 1,5-benzodiazepines are key intermediates for the synthesis of various fused ring systems such as triazolo-, oxadiazolo-, oxazino- or furanobenzodiazepines [5-8]. Besides, benzodiazepine derivatives are also of commercial importance as dyes for acrylic fibers in photography [9]. Owing to their  Molecules 2008, 13 2314 versatile applic