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  • CeCl3·7H2O catalyzed C-C and C-N bond-forming cascade cyclization with subsequent side-chain functionalization and rearrangement: a domino approach to pentasubstituted pyrrole analogues.

CeCl3·7H2O catalyzed C-C and C-N bond-forming cascade cyclization with subsequent side-chain functionalization and rearrangement: a domino approach to pentasubstituted pyrrole analogues.

The Journal of organic chemistry (2012-11-02)
Dipankar Dhara, Krishnanka S Gayen, Saikat Khamarui, Palash Pandit, Sukla Ghosh, Dilip K Maiti
ABSTRACT

CeCl(3)·7H(2)O is found as an efficient catalyst for new intermolecular domino reactions of three-, four- and seven-component assemblies of common precursors under benign reaction conditions. Generation of enaminioesters from β-keto esters and primary amines, activation of their allylic sp(3) C-H, vinylic sp(2) C-H and N-H bonds, multi C-C and C-N bond-forming cascade cyclization with 1,2-diketones and subsequent side-chain alkylation have been developed to construct functionalized pentasubstituted pyrroles and their chiral analogues. The scope of the domino reaction is successfully explored toward synthesis of highly aryl-substituted pyrroles, pentasubstituted pyrroles bearing C2-olefinic side-chain and spiro-2-pyrrolinones and their chiral analogues via unusual side-chain amination, elimination and ring contraction. The new domino reaction is operationally simple, robust, substrate specific, selective and high yielding.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Cerium(III) chloride heptahydrate, 99.9% trace metals basis
Sigma-Aldrich
Cerium(III) chloride heptahydrate, 99.999% trace metals basis
Sigma-Aldrich
Cerium(III) chloride heptahydrate, purum p.a., ≥98.0% (AT)
Sigma-Aldrich
Cerium(III) chloride, AnhydroBeads, −10 mesh, 99.9%
Sigma-Aldrich
Cerium(III) chloride, AnhydroBeads, −10 mesh, ≥99.99% trace metals basis