1.4- Benzodiazepine-2,5-dione libraries

Hulme C, Peng J, Tang S-Y, Bums CJ, Morize I, Labaudiniere R (1998) Improved procedure for the solution phase preparation of 1, 4-benzodiazepine-2, 5-dione libraries via Armstrong s convertible isonitrile and the Ugi reaction. J Org Chem 63 8021-8023... 

C. G. Burow, K. M. Thompson, L. A. Ellman, J. A. Solid-Phase Synthesis of 1,4-Benzodiazepine-2,5-diones. Library Preparation and Demonstration of Synthesis Generality, Boojamra, J. Org. Chem. 1997,62, 1240. 

C Boojamra, K Burow, L Thompson, J. Ellman. Solid-phase synthesis of 1,4-benzodiazepine-2,5-diones. Library preparation and demonstration of synthesis generality. J Org Chem 62 1240-1256, 1997. 

Different novel resin-bound isonitriles have been prepared in order to perform Ugi multicomponent reactions on the solid phase. Thus, Kennedy et al. [346] prepared a novel resin-bound carbonate convertible isonitrile (CCI) that was applied in the preparation of constrained 2,5-diketopiperazine and l,4-benzodiazepine-2,5-dione libraries in parallel 80-well format The first step of the synthetic strategy was a Ugi reaction with a wide variety of amines, aldehydes, and carboxylic acids. Further manipulations of the Ugi MCR products were achieved after basic cleavage from the resin. 

Hui X, Desrivot J, Bories C, Loiseau PM, Franck X, Hocquemiller R, Figadtae B (2006) Synthesis and antiprotozoal activity of some new synthetic substituted quinoxalines. Bioorg Med Chem Lett 16(4) 815-820. doi 10.1016/j.bmcl.2005.11.025 Hulme C, Tang S-Y, Bums CJ, Morize 1, Labaudiniere R (1998) Iminoved procedure for the solution phase preparation of l,4-benzodiazepine-2,5-dione libraries via Armstrong s convertible isonitrile and the Ugi reaction. J Org Chem 63(22) 8021—8023. doi 10.1021/jo980622r Humplett WJ, Lamon RW (1964a) 4-Thiazoline-2-thiones. 1. The Stmcture of intermediate... 

Semiautomated Parallel Synthesis A Library of l,4-Benzodiazepine-2,5-Diones... 

A recent paper by Boojamra et al. (145) rejxMted the synthesis of a 2508-membered SP discrete library L4 of l,4-benzodiazepine-2,5-diones, further exploiting the first... 

While initially the main synthetic interest resided in l,4-benzodiazepin-2-ones [1, 11-13] and l,4-benzodiazepin-2,4-diones [14—18] (and subsequently -2,3-diones ]19] and -2,5-diones ]20]), another l,5-benzodiazepin-2-one system was explored with the strategy outlined in Scheme 3 ]21]. Of particular interest is the role 4-fluoro-3-nitrobenzoic acid, a common fundamental building block central to aU of the the desired structures. Accessing diversity through one or more simple reactants common to aU members of a library has favorable practical consequences on the production phase of a combinatorial Hbrary. 

More recently, a novel resin-bound isonitrile has been reported to be suitable for synthesizing libraries of l,4-benzodiazepine-2,5-diones through Ugi multicomponent reactions [25]. The method produces solid-supported Ugi products, which are cleaved by base activation to form N-acyloxazolidone intermediates that can be further elaborated. The flexibility of the approach was demonstrated by an analogous preparation of 2,5-diketopiperazines by simply replacing the 2-aminobenzoyl building blocks with a-amino acids. 

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