Synthesis of Substituted 2-Aminoimidazoles via Pd-Catalyzed Alkyne Carboamination Reactions. Application to the Synthesis of Preclathridine Natural Products | Zendy

Blane P. Zavesky | Zendy; Nicholas R. Babij | Zendy; John P. Wolfe | Zendy

Open Access

Synthesis of Substituted 2-Aminoimidazoles via Pd-Catalyzed Alkyne Carboamination Reactions. Application to the Synthesis of Preclathridine Natural Products

Author(s) -

Blane P. Zavesky,

Nicholas R. Babij,

John P. Wolfe

Publication year - 2014

Publication title -

organic letters

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.94

H-Index - 239

eISSN - 1523-7060

pISSN - 1523-7052

DOI - 10.1021/ol502471x

Subject(s) - chemistry , alkyne , propargyl , annulation , catalysis , aryl , combinatorial chemistry , reaction conditions , organic chemistry , alkyl

A new method for the synthesis of 2-aminoimidazole products is described. The heterocyclic products are generated in good yields via Pd-catalyzed carboamination reactions of N-propargyl guanidines and aryl triflates. This methodology generates both a C-N and C-C bond during the annulation step and facilitates the rapid construction of 2-aminoimidazole products with different aryl groups. The utility of this methodology was demonstrated in the total synthesis of preclathridine A, preclathridine B, and dorimidazole B from a single intermediate.

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