By Moody C.J.

ISBN-10: 0762302097

ISBN-13: 9780762302093

This quantity encompasses a variety of issues equivalent to the activation and manipulation of pyrroles, the synthesis of annelated pyrroles utilizing acylation reactions and the synthesis of kainoids, a kin of hugely biologically energetic nitrogen heterocycles.

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This quantity features a diversity of issues resembling the activation and manipulation of pyrroles, the synthesis of annelated pyrroles utilizing acylation reactions and the synthesis of kainoids, a relations of hugely biologically energetic nitrogen heterocycles.

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Taube, H. J. Am. Chem. Soc. 1989, 111, 5969. 11. (a) Myers, W. ; Harman, W. D. J. Am. Chem. Soc. 1991, 113, 6682. (b) Myers, W. ; Koontz, J. ; Harman, W. D. J. Am. Chem. Soc. 1992, 114, 5684. 12. (a) Hodges, L. ; Koontz, J. ; Myers, W. ; Harman, W. D. J. Org. Chem. 1993, 58, 4788. (b) Hodges, L. ; Koontz, J. ; Myers, W. ; Harman, W. D. J. Org. Chem. 1995, 60, 2125. 13. (a) Hodges, L. ; Moody, M. ; Harman, W. J. Am. Chem. Soc. 1994,116, 7931. (b) Hodges, L. ; Spera, M. U; Moody, M. ; Harman, W.

8 1 2 MeCN Me2CO 3 4 5 6 2 M LiOTf (DME) MeOH DMF DMAc 7 8 NMF DMSO 6 5 DMPU 5 M LiOTf (DME) 5 5 9 10 Osmium Activation of Pyrroles 25 and/or ring opening (vide infra). 12'14An exception to this is the reaction of 26 with N-phenylmaleimide. This cycloaddition is moderately accelerated and affords a cleaner product when carded out in the presence of TMSOTf (see Figure 16). Competing p-Michael Additions Under certain circumstances, the conjugate addition and cycloaddition reaction pathways overlap for t~,~-unsaturated electrophiles.

Under certain circumstances, rl2-pyrroles undergo clean and facile dipolar cycloaddition reactions with dipolarophiles to allow a viable entry into the azanorbomane ring system. Finally, the synthesis of several classes of functionalized 13-vinylpyrrole complexes allows a fast entry into the synthesis of indoles, where a high degree of functional flexibility is obtainable on the six-membered ring. While regioselective nucleophilic addition and a few examples of electrophilic substitutions with ~ - and rlS-pyrrolyl complexes have been reported, rl2-binding represents a novel, highly versatile binding mode allowing controlled, synthetically useful transformations to be achieved with this aromatic heterocycle.

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


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