147088-90-2

Upstream product

• 55895-62-0 2-(4-methylbenzoyl)pyrrole 
• 874-60-2 4-methyl-benzoyl chloride 
• 117378-85-5 (1H-pyrrol-3-yl)-(4-methylphenyl)-ketone 
• 147089-54-1 2,4-Bis-(2-p-tolyl-benzo[1,3]dithiol-2-yl)-1H-pyrrole 
• 109-97-7 pyrrole 
• 147089-33-6 4-(2-p-Tolyl-benzo[1,3]dithiol-2-yl)-2-(2-p-tolyl-benzo[1,3]oxathiol-2-yl)-1H-pyrrole 
• 147089-17-6 1-Benzenesulfonyl-3-(2-p-tolyl-benzo[1,3]dithiol-2-yl)-1H-pyrrole 
• 147089-25-6 3-(2-p-Tolyl-benzo[1,3]dithiol-2-yl)-1H-pyrrole 
• 97188-29-9 1-(phenylsulfonyl)-3-(4-methylbenzoyl)pyrrole 
• 147089-43-8 p-Tolyl-[4-(2-p-tolyl-benzo[1,3]dithiol-2-yl)-1H-pyrrol-2-yl]-methanone 
• 147089-07-4 p-Tolyl-[5-(2-p-tolyl-benzo[1,3]dithiol-2-yl)-1H-pyrrol-3-yl]-methanone 

Downstream Products

• 321899-67-6 2,4-bis(p-methylphenylhydroxymethyl)pyrrole 
• 321899-74-5 5,10-ditolyl-8-aza-16-carba-5,10,15,17-tetrahydrotripyrrane 

Relevant academic research and scientific papers

Inverted meso-aryl porphyrins with heteroatoms; characterization of thia, selena, and oxa N-confused porphyrins

Synthesis and characterization of inverted porphyrins containing S, Se, and O are reported. A simple 3 + 1 MacDonald-type condensation using modified tripyrrane containing the N-confused ring and diols afforded various N-confused porphyrins 6a-f in 19-30% yield. The single-crystal X-ray structure of 6b shows a ruffled conformation with tilt angles of 21.11° and 31.23° for the N-confused ring and the adjacent pyrrole ring III, respectively, revealing its severe nonplanarity. Significant changes in Cα-Cβ, Cβ-Cβ, and Cα-X bond lengths are observed in 6b relative to free thiophene and pyrrole, suggesting the altered delocalization pathway in the modified N-confused porphyrins. The two molecules in the unit cell show a cyclophane-type noncovalent dimer with a face to face orientation of two N-confused pyrrole rings as a result of the presence of weak N-H···N and C-H···N intermolecular hydrogen bonds involving pyrrole-NH, the N atom of the N-confused ring, and the C atom of the pyrrole ring. A detailed 1H and 13C NMR study by 1D and 2D methods allowed assignments of all the peaks in the free base and protonated forms. NMR studies reveal the presence of three different tautomeric forms in solution for 6c in CDCl3 at low temperature. UV-visible studies reveal absorption band shifts upon heteroatom substitution, and the magnitudes of these shifts are dependent on the nature of the heteroatom. In all cases both monoprotonated and diprotonated species have been identified, and on addition of acid, the first proton goes to the outer N2 atom of the N-confused ring.

General Methods for Synthesizing 2,4-Diacylpyrroles and their Precursors Containing One or Two Masked Acyl Groups

A thorough study of the synthesis of 2,4-diacylpyrroles by direct acylation of pyrrole and 2- and 3-acylpyrroles is reported.Among these, Friedel-Crafts acylation of 3-acylpyrroles is the most general and advantageous method because it utilises easily accessible starting materials.In addition it is always regiospecific and readily provides 2,4-diacylpyrroles containing identical or different acyl groups in very high yields (81-100percent) under mild conditions, Alternative procedures concern the synthesis of precursors of 2,4-diacylpyrroles containing one or two acyl groups masked by a 1,3-benzodithiolyl or 1,3-benzoxathiolyl group and subsequent hydrolysis with HgO-35percent aq.HBF4-Me2SO.Overall yields are always good (52-60percent).Indirect acylation constitutes a secure complement to direct acylation when it is necessary to operate in the presence of protected acyl groups.