84080-62-6Relevant academic research and scientific papers
A general route for the synthesis of flexible porphyrin dimers
Twyman, Lance J.,Sanders, Jeremy K. M.
, p. 6681 - 6684 (1999)
The synthesis of two cyclic porphyrin dimers is reported. In each case the porphyrins are connected by a rigid butadiyne link, and a flexible alkyl chain tether. The length of this tether controls both the porphyrin-porphyrin distance, and porphyrin-porphyrin geometry. It is hoped that the extra flexibility designed within these molecules will enable them to act as general catalytic hosts for future study.
Porphyrins with exocyclic rings. Part 21: Influence of pyrrolic and carbocyclic ring alkyl substituents on the synthesis of porphyrins bearing six-membered exocyclic rings
Shiner, Craig M.,Lash, Timothy D.
, p. 11628 - 11640 (2007/10/03)
A series of 5-substituted 4,5,6,7-tetrahydroindoles were prepared by reacting 4-substituted cyclohexanones with phenylhydrazones derived from esters of acetoacetic acid under Knorr-type reaction conditions. Related 6,6-dimethyltetrahydroindoles were also
Diastereoselective reduction of E and Z α-alkoxyimino-β-ketoesters by sodium borohydride
Correa Jr., Ivan R.,Moran, Paulo J. S.
, p. 14221 - 14232 (2007/10/03)
The reduction of (Z)-α-alkoxyimino-β-ketoesters, R1COC(= NOR3)CO2R2 (R1 = Me, Et, MeOCH2, Ph; R2 = Me, Et, PhCH2; R3 = Me, PhCH2) with NaBH4
Porphyrins with exocyclic rings. Part 10.1 Synthesis of meso,β- propanoporphyrins from 4,5,6,7-tetrahydro-1H-indoles
Lash, Timothy D.
, p. 359 - 374 (2007/10/03)
Benzyl (6) and tert-buty1 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.
