A New Pyrrole Synthesis via Silver(I)-Catalyzed Cycloaddition of Vinylogous Diazoester and Nitrile

Abstract

A new synthesis of di- and trisubstituted pyrroles was achieved by treating in situ generated vinylogous diazoesters and readily available nitriles with a catalytic amount of silver(I) antimony hexafluoride at room temperature. This method showcased the potential of utilizing silver(I) carbenoids in preparing heterocyclic compounds.

Regioselective Synthesis of Functionalized Pyrroles via Gold(I)‐Catalyzed [3+2] Cycloaddition of Stabilized Vinyl Diazo Derivatives and Nitriles

“…Many of the methods for preparing functionalized pyrroles, among them the classical Hantzsch or Knorr synthesis, rely on the use of [3+2] cyclocondensation reactions between appropriate substrates (Scheme a). Surprisingly, the reaction of simple nitriles toward C 3 synthons in [3+2] cyclization reactions has been little explored 3–5. However, nitriles are especially attractive as partners for formal [3+2] cycloaddtions because of the great number of nitriles that are commercially available and, consequently, the development of such approaches would be very interesting from a synthetic point of view.…”

Synthesis of Highly Substituted Pyrrole and Dihydro‐1H‐Pyrrole Containing Barbituric Acids via Catalyst‐Free One‐Pot Four‐Component Reactions

“…There are other methodologies for the construction of pyrroles by using metal or base‐catalyzed MCRs. Examples include gold , titanium , ruthenium , AgSbF 6 , silver , and n ‐BuLi catalyzed reactions. Nonetheless, most of the synthetic approaches toward pyrrole synthesis suffer from disadvantages such as using either expensive toxic metal catalyst and base or harsh reaction conditions.…”

Clauson Kaas Pyrrole Synthesis Catalyzed by Acidic Ionic Liquid under Microwave Irradiation

“…They are also very useful starting materials for biologically important compounds such as indolizidine alkaloids, bicyclic lactams, and unsaturatedlactams [4][5][6][7]. Various pyrrole syntheses have been reported in the literature [8][9][10][11][12][13][14][15]. One of these methods is Clauson Kaas pyrrole synthesis which uses 2,5-dimethoxytetrahydrofuran as four-carbon source.…”