Michael Addition of Imines to Alkynylcarbene Complexes with Subsequent Intramolecular Cyclization ‐ An Efficient Three‐Step Synthesis of 2 H ‐Pyrroles | Zendy

Funke Frank | Zendy; Duetsch Michael | Zendy; Stein Frank | Zendy; Noltemeyer Matthias | Zendy; Meijere Armin De | Zendy

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Michael Addition of Imines to Alkynylcarbene Complexes with Subsequent Intramolecular Cyclization ‐ An Efficient Three‐Step Synthesis of 2 H ‐Pyrroles

Author(s) -

Funke Frank,

Duetsch Michael,

Stein Frank,

Noltemeyer Matthias,

Meijere Armin De

Publication year - 1994

Publication title -

chemische berichte

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.667

H-Index - 136

eISSN - 1099-0682

pISSN - 0009-2940

DOI - 10.1002/cber.19941270520

Subject(s) - chemistry , carbene , chromium , intramolecular force , tetrahydrofuran , medicinal chemistry , michael reaction , aldimine , intramolecular reaction , stereochemistry , polymer chemistry , organic chemistry , catalysis , solvent

Imines 7 , 11–13 were added to (1‐alkynylcarbene)chromium complexes 6a–d to form {[2‐(methyleneamino)ethenyl]‐carbene}chromium complexes 8a–d , 14a–d , 15a–d , 16a–d in good to very good yields (63–98%) except for two cases (41–59%). The carbene ligands of the latter compounds cyclize to 2 H ‐pyrroles 9a–d , 17a–d , 18a–d , 19a–d upon heating in tetrahydrofuran solution to 50–55°C.

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