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Advances in Nitrogen Heterocycles, Volume 3 by Moody C.J.

By Moody C.J.

This quantity encompasses a diversity of subject matters resembling the activation and manipulation of pyrroles, the synthesis of annelated pyrroles utilizing acylation reactions and the synthesis of kainoids, a family members of hugely biologically lively nitrogen heterocycles.

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50 1. /-Pr2EtN 2. HOTf ~ Me Me i N+ _( ~ ~ ~ a'~Os H 141 Me a ~N~ DBU H2 % -os H 142 trapped in situ with dienophile Figure 25. Synthesisof 13-vinylpyrroleand 2-azafulvenium complexes via aldol reactions. presumably goes through an intermediate 2-azafulvenium complex, and protonation of the isolated vinylpyrrole complexes gives the highly stable 2-azafulvenium complexes 135-140 in good yield. , 132 and 133) are often isolated. In the case of the vinylpyrrole complex 130, derived from 21 and 3-pentanone, a single isomer is formed with the methyl and ethyl substituents having a relative cisstereochemistry.

Because attempts to remove the benzyl groups from 15 proved futile, 15 design of a new protection strategy was necessary if a viable route to rigidin was to be realized. In view of some of the difficulties in removing heterocyclic nitrogenprotecting groups, ~6it was felt that acid-labile groups such as benzyloxymethyl (BOM) 17a for the uracil-type nitrogens and an electron-rich benzyl g r o u p ]7b at the pyrrole nitrogen would provide the most flexible Synthesis of [b]-Annelated Pyrroles 51 and efficient deprotection scheme.

Palmer, J. ; Morgan, S. E. J. Chem. Soc. Perkin Trans. 11990, 3212. ;1Leusen, A. M. J. Org. Chem. 1992, 57, 2245. For a review of 13-substituted pyrrole syntheses, see: Anderson, H. ; Loader, C. E. Synthesis 1985, 353, and references therein. 3. Bray, B. ; Mathies, P. ; Solas, D. ; Tidwell, T. ; Artis, D. ; Muchowski, J. M. J Org. Chem. 1990, 55, 6317, and references therein. 4. ; Trudell, M. L. Chem. Rev. 1996, 96, 1179, and references therein. 5. For a review of rlS-pyrrole complexes, see: (a) Zakrzewski, J.

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