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Application of vinylogous carbamates and vinylogous aminonitriles to the regiospecific synthesis of uniquely functionalized pyrroles and quinolones

Author:
Gupton, John T., Crawford, Evan, Mahoney, Matt, Clark, Evan, Curry, Will, Lane, Annie, Shimozono, Alex, Moore-Stoll, Veronica, Elofson, Kristen, Juekun, Wen, Newton, Micah, Yeudall, Scott, Jaekle, Elizabeth, Kanters, Rene, Sikorski, James A.
Source:
Tetrahedron 2018 v.74 no.52 pp. 7408-7420
ISSN:
0040-4020
Subject:
bioactive compounds, carbamates, chemical reactions, chemical structure, pyrroles, quinolones, regioselectivity
Abstract:
Pyrroles and quinolones represent core structures, which are routinely found in both natural and synthetic bioactive substances. Consequently, the development of efficient and regiospecific methods for the preparation of such heterocycles with unique functionality is of some importance. We describe herein the regiospecific synthesis of 1,2,3,4-tetrasubstituted pyrroles containing polar substituents and such products are prepared from vinylogous carbamates and vinylogous aminonitriles. We also describe the regiospecific synthesis of 3-aryl containing 1,3,6-trisubstituted quinolones from vinylogous carbamates. The use of an amine exchange reaction to prepare precursors for the pyrrole and quinolone forming cyclizations represents a key factor in the strategy.
Agid:
6232090