Pyrrolo 3,4-fc pyridines

CN 1 -Cyclopropyl-6-fluoro-1,4-dihydro-8-methoxy-7-[(4a5,7a5)-octahydro-6//-pyrrolo[3,4-fc]pyridin-6-yl]-... 

Furthermore, oxazoles of type 9-82 bearing a secondary amino functionality can be converted into pyrrolo[3,4-b]pyridines 9-86 by reaction with appropriate acid chlorides 9-83 in a triple domino process consisting of amide formation/hetero Diels-Alder reaction and retro-Michael cycloreversion via 9-84 and 9-85 (Scheme 9.17). The pyrrolo[3,4-fc]pyridines can be obtained in even higher yields when the whole sequence is carried out as a four-component synthesis in toluene. Here, 1.5 equiv. NH4C1 must be added for the formation of the now intermediate oxazoles [56b]. 

Pyrrolo[3,2-c]pyridine, 4-hydroxy-tautomerism, 4, 500 Pyrrolo[3,2-c]pyridine, 2,3,3-trimethyl-methylation, 4, 513 Pyrrolo[3,4-fc]pyridine, 2-methyl-UV spectra, 4, 501 Pyrrolo[3,4-c]pyridine, 2-methyl-UV spectra, 4, 501 Pyrrolopyridines acylation, 4, 504 bromination, 4, 505 diazo coupling, 4, 506 NMR, 4, 498... 

Pyrrolo[2,3-fc]pyridinium iodide, 1,7-dimethyl-reduction, 4, 508 Pyrrolo[3,2-fc]pyridin-2-ones spectra, 4, 502... 

Pyrrolo[3,4-d]pyridazinium salts, 2,3-dimethyl-synthesis, 4, 291 Pyrrolo[l, 2- fcjpyridazinones oxidation, 4, 298 Pyrrolo[2,3-fc]pyridine, 1-acetyl-cycloaddition reactions, 4, 509 Pyrrolo[2,3-fc]pyridine, 3-bromo-nitration, 4, 505... 

B.ii.e Carbonylation and Acylation. The keto function in pyrrolo[3,2-c]pyridin-4-ones and pyrido[3,4- ]pyrrolizidin-l-ones can be enolized and triflated to yield the substrates 72 and 73, respectively (Scheme 34). Replacement of the triflyloxy group by carbonylation is effected with palladium catalysis. Reaction of the pyrido[3,4-fc]-pyrrolizidin-l-ones 73 was complicated by formation of a by-product, namely, the 2-methoxy adduct 74. In the latter case competitive palladium-assisted elimination of the triflyloxy group leads to an imminium intermediate, which adds a methoxy group as a... 

A further synthesis of thieno[2,3-6]pyridines (79JHC603) resembles quite closely the preparation of pyrrolo[2,3-fc]pyridines (76AP597). 2-Amino-3-cyanothiophenes (e.g. 268 Scheme 62) were reacted with ethyl aminocrotonate to give enamines, which were cyclized with sodium ethoxide yielding 4-aminothieno[2,3-5]pyridines. 

Pyrrolo[2,3-fc]pyridine, 2,3-dihydro-electrophilic substitution, 4, 503 nitration, 4, 512 synthesis, 4, 520... 

Pyrrolo[2,3-fc]pyridme, 6-methyl-reaction with aldehydes, 4, S03 reaction with benzaldehyde, 4, 511 Pyrrolo[2,3-fc]pyridine, 7-methyl-hydrogenation, 4, 508 Pyrrolo[2,3-fc]pyridine, 3-nitro-2-phenyl-reduction, 4, 511 Pyrrolo[2,3-fc]pyridine, 2-phenyl-nitrosation, 4, 506 quatemization, 4, 503 synthesis, 4, 522... 

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