75400-63-4

Upstream product

• 7697-46-3 phenyl(1H-pyrrol-2-yl)methanone 
• 98-88-4 benzoyl chloride 
• 1468-28-6 4-benzoylmorpholine 
• 611-74-5 N,N-dimethylbenzamide 
• 1003-29-8 2-pyrrole aldehyde 
• 100-58-3 phenylmagnesium bromide 

Downstream Products

• 107798-98-1 5-phenyldipyrromethane 
• 917-23-7 5,15,10,20-tetraphenylporphyrin 
• 67605-65-6 5,10,15-tris(phenyl)-20-(4-nitrophenyl)porphyrin 

Relevant academic research and scientific papers

Efficient synthesis of bis(heterocyclyl)methanes

The reaction of pyrrole/furan aldehyde with Grignard reagent and pyrrole/N-methyl pyrrole in sequence allows efficient synthesis of a number of meso-elaborated bis(heterocyclyl)methanes, which are otherwise difficult to obtain through a direct aldehyde co

Nuclear magnetic resonance spectroscopical studies of 2-carbonyl derivatives of five-membered monohetero-cycles and determination of aromaticity indices

1H And 13C chemical shifts of formyl, acetyl, benzoyl, and methoxycarbonyl derivatives of benzene, thiophene, pyrrole and furan in chloroform-d, methanol-d4, and DMSO-d6 are examined. Deviation of the signals of the ring protons and carbonyl carbons provide bases for estimating the indices of aromaticity of the heterocycles. The exceptionally large carbonyl stretching vibration of furan derivatives and correlations of the stretching frequencies with the reactivities of the carbonyl groups are discussed.

One-flask synthesis of meso-substituted dipyrromethanes and their application of the synthesis of trans-substituted porphyrin building blocks

The reaction at room temperature of an aldehyde with excess pyrrole in the absence of solvent affords the meso-substituted dipyrromethane. The reaction is catalyzed with trifluoroacetic acid or with BF3·O(Et)2. The dipyrromethane is purified by crystallization or by flash chromatography on silica with eluants containing 1% triethylamine. The reaction is compatible with aliphatic or aromatic aldehydes, including 2,6-disubstituted benzaldehydes. Nine dipyrromethanes have been prepared in this manner in yields of 47-86%, indicating the broad scope of the reaction. The dipyrromethanes are stable in the purified form in the absence of light and air. Similar reaction with terephthalaldehyde and pyrrole affords the corresponding bis-dipyrromethane. The reaction of a meso-substituted dipyrromethane with an aldehyde under the conditions of the two-step one-flask porphyrin synthesis affords a direct route to trans-substituted meso-porphyrins. Acidolysis of the dipyrromethane is negligible under the conditions of the porphyrin-forming reaction. Four porphyrins bearing peripheral functional groups and facially-encumbering groups have been prepared which serve as key building blocks in the synthesis of linear porphyrin arrays.

Antifungal agents, II: Synthesis and antifungal activities of aryl-1H-pyrrol-2-yl-1H-imidazol-1-yl-methane derivatives with unsaturated chains

The synthesis and antifungal activities of aryl-1H-pyrrol-2-yl-1H-imidazol-1-yl-methanes having allyl, crotyl, and acrylate chains linked to the N-pyrrole atom and substituted at phenyl ring by Cl, F, CH3, and NO2 groups are reported

A NEW ROUTE FOR MESO-SUBSTITUTED PORPHYRIN

A new synthetic route of meso-substituted porphyrins was esthablished.The method presented here shows wide applicability for the preparation of aryl and alkyl meso-substituted porphyrins.

Notes on the Synthesis of meso-Substituted Porphyrins from Pyrryl Carbinols and the Mechanism of the Rothemund Reaction

Aryl pyrryl carbinols have been found to readily cyclize to meso-substituted tetraarylporphyrins in yields which are consistent with the intermediacy of the pyrryl carbinols in the Rothemund reaction.Acidic solutions of the pyrryl carbinols show absorption bands characteristic of pyrrolylmethenes.It is suggested that pyrrolylmethenes are likely intermediates in the Rothemund reaction.