Cu(I)-catalyzed intramolecular cyclization of ene-carbamates: synthesis of indoles and pyrrolo[2,3-c]pyridines

Transition metals in organic synthesis: Highlights for the year 2005

“…Copper catalyzed intermolecular N-alkenylations of amides with alkenyl iodides [571] used in a synthesis of lobatamide analogs [52] and N-allenylation of amides, carbamates, and ureas using allenyl halides [572,573]. Copper catalyzed intramolecular couplings of amides with aryl halides [574] and this type of reaction was used in a synthesis of reblastatin (Eq. (64)) [575].…”

Synthesis and Biological Activities of Azalamellarins

“…Lactams occur in a wide range of synthetic and natural product derivatives, many of which have potential uses as pharmacologically active compounds. [6] This useful pharmacophore has attracted much interest specifically for its use as an antitumor and anticancer agent. [7] Oxynitidine (3), a benzo [c]phenanthridine alkaloid from Xanthoxylum (Rutaceae), has been investigated as a potential antitumor and antiviral agent (Scheme 1).…”

Transition Metal‐Catalyzed Synthesis of Fused Five‐Membered Aromatic Heterocycles

“…The same group recently provided a possible solution to this problem by developing a very efficient complementary approach toward the indole ring synthesis, where aryl azides were employed as electrophilic nitrogen sources. In this way, ortho-vinyl-substituted aryl azides 208, It was shown that the intramolecular N-arylation of ene-carbamates 216 in the presence of the Cu(I)-L-proline catalytic system and an external inorganic base could provide N-protected indole-3-carboxylate derivatives 217 (Scheme 9.78) [232]. In the case of substrates bearing electron-deficient substituents on the aryl ring, partial deprotection of the Cbz-group accompanied the formation of the corresponding products.…”