Application of Vinylogous Carbamates and Vinylogous Aminonitriles to the Regiospecific Synthesis of Uniquely Functionalized Pyrroles and Quinolones

Overview

Journal Tetrahedron

Specialty Chemistry

Date 2019 Jul 11

PMID 31289413

Citations 2

Authors

John T Gupton

Evan Crawford

Matt Mahoney

Evan Clark

Will Curry

Annie Lane

Alex Shimozono

Veronica Moore-Stoll

Kristen Elofson

Wen Juekun

Micah Newton

Scott Yeudall

Elizabeth Jaekle

Rene Kanters

James A Sikorski

Affiliations

Soon will be listed here.

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 1,3,6trisubstituted 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.

Citing Articles

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Rustin G, Donahue M Tetrahedron Lett. 2023; 122.

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Silica gel and microwave-promoted synthesis of dihydropyrrolizines and tetrahydroindolizines from enaminones.

Klintworth R, Morgans G, Scalzullo S, de Koning C, van Otterlo W, Michael J Beilstein J Org Chem. 2021; 17:2543-2552.

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