Iron(III) chloride as mild catalyst for the dearomatizing cyclization of N-acylindoles

A catalytic approach for the preparation of indolines by dearomatizing cyclization is presented. FeCl3 acts as a catalyst to afford tetracyclic 5a,6-dihydro-12H-indolo[2,1-b][1,3]benzoxazin-12-ones in good yields. The cyclization also proceeds with tosylamides forming C-N bonds in 53 % yield. peerReviewed

Synthesis of Polycyclic Indolines by Utilizing a Reduction/Cyclization Cascade Reaction

European journal of organic chemistry 2021(45), 6097-6101 (2021). doi:10.1002/ejoc.202101191

Iron(III) Chloride as a Mild Catalyst for the Dearomatizing Cyclization of N-Acylindoles

A catalytic approach for the preparation of indolines by dearomatizing cyclization is presented. FeCl3 acts as a catalyst to afford tetracyclic 5a,6-dihydro-12H-indolo[2,1-b][1,3]benzoxazin-12-ones in good yields. The cyclization also proceeds with tosylamides forming C-N bonds in 53% yield.

Synthesis of N‐Fused Indolines via Copper (II)‐Catalyzed Dearomatizing Cyclization of Indoles

Advanced synthesis & catalysis 363(12), 3121-3126 (2021). doi:10.1002/adsc.202100290

Synthesis of Polycyclic Indolines utilizing a reduction/cyclization cascade reaction

Subsequent reduction and dearomatizing cyclization reactions open up an entry into the synthesis of novel N-fused polycyclic indolines. The dearomatizing cyclization as key step of the sequence proceeds well with Cu(OTf)2 or TfOH as catalyst. At elevated temperature reduction of nitro-substituted precursors with iron under acidic conditions affords a broad variety of polycyclic indolines directly in a two-step cascade reaction in good to excellent yields. Using the developed protocol, the alkaloids Tryptanthrin and Phaitanthrin C have been prepared. peerReviewed

Cover Feature: Synthesis of Polycyclic Indolines by Utilizing a Reduction/Cyclization Cascade Reaction (Eur. J. Org. Chem. 45/2021)

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