First synthesis of pyrrolo[1,2:1′,2′]azepino[5,6-b]indole derivatives (original) (raw)

2003, Tetrahedron Letters

The synthesis of 1,2,3,6,6a,7-hexahydro-7-methyl-5-imino-1H-pyrrolo[1,2-c]imidazolo[5,4-b]indole

Arkivoc, 2009

This paper is dedicated to Henk van der Plas who has for many years inspired heterocyclic chemists the world over with his innovative research, his impeccable standards and his charming personality Abstract N-3-(1-Methylindol-3-yl)propan-N-(2,2,2-trichloroethoxysulfonyl)guanidine was synthesized from 3-formyl-1-methylindole in six steps and subjected to conditions intended to convert the side-chain into a 2-iminotetrahydropyrimidine-containing product, of relevance to a possible synthesis of the aplicyanins. An alternative reaction course was observed, resulting in the formation of a new tetracyclic system.

Synthesis of the new ring system pyrrolizino[2,3-b]indol-4(5H)-one

Tetrahedron, 2011

Derivatives of the new ring system pyrrolizino[2,3-b]indol-4(5H)-one were prepared in four steps starting from substituted benzonitriles bearing a functionalized amino group in the adjacent position. The unsubstituted-and the dimethoxy-pyrrolizinoindolones 5a and 5b exhibited modest activity against the HL-60(TB) human leukemia cell line, whereas the N-methylated dimethoxy-pyrrolizinoindolone 6b showed to be selective against MOLT-4 leukemia, A549/ATCC, HOP-92, and NCI-H460 non-small cell lung cancer, and CAKI-1 renal cancer cell lines.

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4′-Methyl-1 H -14′,19′-dioxa-4′-azaspiro[indole-3,5′-tetracyclo[18.4.0.0 2,6 .0 8,13 ]tetracosane]-1′(24′),8′,10′,12′,20′,22′-hexaene-2,7′(3 H )-dione

Acta Crystallographica Section E Structure Reports Online, 2012