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- W2950871845 abstract "Abstract Benzyl (6) and tert-butyl 3-methyl-4,5,6,7-tetrahydro-1H-indole-2-carboxylates (28) were easily prepared from cyclohexanone using a variation of the Knorr pyrrole condensation. Regioselective oxidation with lead tetraacetate gave the corresponding 7-acetoxy derivatives, or related solvolysis products, and subsequent reaction with 5-unsubstituted pyrrole-2-carboxylates in the presence of p-toluenesulfonic acid in acetic acid gave a series of 7-pyrrolyltetrahydroindoles 16 in excellent overall yields. Cleavage of the protective ester units, followed by acid-catalyzed condensation with diformyldipyrrylmethanes 19 under modified MacDonald “2 + 2” conditions gave good yields of meso,β-propanoporphyrins 26. This chemistry was sufficiently versatile that a porphyrin with two six-membered exocyclic rings (34) could be prepared by the same methodology. On the other hand, attempts to cyclize an a,c-biladiene 37 incorporating a six-membered carbocyclic ring gave moderate to poor yields of the required meso,β-propanoporphyrin 26a, probably due to a deleterious steric interaction between the carbocyclic ring and an adjacent alkyl substituent. Nonetheless, the results described below demonstrate the value of this approach for the synthesis of sedimentary cycloalkanoporphyrins" @default.
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- W2950871845 date "1998-01-01" @default.
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- W2950871845 title "Porphyrins with exocyclic rings. Part 10. Synthesis of meso,β-propanoporphyrins from 4,5,6,7-tetrahydro-1H-indoles" @default.
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- W2950871845 doi "https://doi.org/10.1016/s0040-4020(97)10288-5" @default.
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