Hydantoins, fused-tricyclic

Fluorous Mixture Synthesis of Fused-Tricyclic Hydantoins. 114... 

Fig. 32 Fluorous mixture synthesis of fused-tricyclic hydantoins. Reagents and conditions a Mo(CO)6, DMSO, toluene, MW 150 °C, 35 min, closed system b TFA CH2CI2 (1 1), rt c PhC2H4NH2, PyBOP, i-Pr2EtN, MeOH, CH2CI2 followed by flash chromatography and F-HPLC d i-Pr2EtN, MeOH, MW 140 °C, 40 min, followed by F-SPE...

In addition to the en route protocol described in Section 13.2.6 for the synthesis of pas-sifloricins, the use of redundant tags for the synthesis of fused-tricyclic hydantoins is another example of FMS in which the number of fluorous tags is less than that of components in the mixture. Since molecules for FMS have fluorine atoms both on the parent structure and on the tag, each component in the mixture has different total fluorine content - even the tag may be redundant. 

Manku, S. and Curran, D. P. (2005) Fluorous mixture synthesis of fused-tricyclic hydantoins. Use of a redundant tagging strategy on fluorinated substrates../. Org. Chem., 70, 4470-4473. 

W. Zhang, Y. Lu, C.H. Chen, D.P. Curran, Fluorous synthesis of hydantoin-, piperazinedione-, and benzodiazepinedione-fused tricyclic and tetracyclic ring systems, Eur. J. Org. Chem. (2006) 2055-2059. 

Fluorous aminoesters have also been used in DOS of three unique triaza tricyclic and tetracyclic ring systems (Scheme 22) [44], Bicyclic pyrrolidines 12 generated from one-pot, three-component 1,3-dipolar cycloaddition of azomethine ylides were further converted to hydantoin-, piperazinedione-, and benzodiazepine-fused compounds 31-33, respectively. Each of these three heterocyclic scaffolds has four stereocenters on the central pyrrolidine ring and up to four points of diversity (R1 to R4). The structure of compound... 

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