92399-34-3Relevant academic research and scientific papers
New syntheses of pyrrolo[3,4-b]indoles, benzo[b]furo[2,3-c]pyrroles, and benzo[b]thieno [2,3-c]pyrroles utilizing the reaction of münchnones (1,3-oxazolium-5-olates) with nitroheterocycles
Gribble, Gordon W.,Pelkey, Erin T.,Switzer, Frank L.
, p. 1061 - 1062 (2007/10/03)
1,3-Dipolar cycloaddition of münchnones (mesoionic 1,3-oxazolium-5-olates) 3 and 4 with 2- and 3-nitroindoles, 2-nitrobenzo[b]furan, and 3-nitrobenzo[b]thiophene affords the corresponding pyrrolo[3,4-b]indoles, benzo[b]furo[2,3-c]pyrroles, and benzo[b]thi
Synthesis and Diels-Alder Reactions of 1,3-Dimethyl-4-(phenylsulfonyl)-4H-furoindole. A new Annulation Strategy for the Construction of Ellipticine and Isoellipticine
Gribble, Gordon W.,Saulnier, Mark G.,Sibi, Mukund P.,Obaza-Nutaitis, Judy A.
, p. 4518 - 4523 (2007/10/02)
The novel fused heterocycle 1,3-dimethyl-4-(phenylsulfonyl)-4H-furoindole (4) is synthesized from 3-ethylindole (6) in six steps (46percent yield) or from indole-3-carboxaldehyde (12) in four steps (21percent yield).Furoindole 4 undergoes Diels-Alder reactions with dimethyl acetylenedicarboxylate, N-phenylmaleimide, benzyne, and 3,4-pyridyne (5) to give the expected adducts 17, 18a,b, 19, and 23a,b, respectively.Deoxygenation and desulfonylation of 19 and 23a,b, respectively, give benzocarbazole 22 and a readily separable mixture of the pyridocarbazole alkaloids ellipticine (1a) and isoellipticine (2a).
