The synthesis of indolo- and pyrrolo[2,1-a]isoquinolines
The synthesis of fused isoquinolines from N-benzyl protected indoles and pyrroles is described. For example, treatment of t-butyl-2-(2-formyl-3,4- dihydro-1-naphthalenyl)-3-methyl-1H-indole-1-carboxylate with KOBut in DMF provided 14-methyl-8-phenylbenzo[h]indolo[2,1-a]isoquinoline in good yield. Analogous N-benzylpyrrole precursors could similarly be cyclized to give pyrrolo[2,1-a]isoquinolines.
De Koning, Charles B.,Michael, Joseph P.,Pathak, Rakhi,Van Otterlo, Willem A.L.
Synthesis of the dibenzopyrrocoline alkaloid skeleton: indolo[2,1-a]isoquinolines and related analogues
The indolo[2,1-a]isoquinoline and pyrrolo[2,1-a]isoquinoline nuclei have been synthesized from N-benzylindole or ethyl 1H-indol-1-ylacetate and N-benzylpyrrole precursors, respectively. Firstly, at C-2 of either the indole or pyrrole nucleus, aromatic rin
L?tter, Angelique N.C.,Pathak, Rakhi,Sello, Thato S.,Fernandes, Manuel A.,van?Otterlo, Willem A.L.,de Koning, Charles B.
p. 2263 - 2274
(2007/10/03)
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