16200-52-5Relevant academic research and scientific papers
A General Synthesis of Pyrroles from Aldehydes and Ketones
Baldwin, Jack E.,Bottaro, Jeffrey C.
, p. 624 - 625 (1982)
The azines of enolisable aldehydes and ketones are converted into pyrroles via thermal rearrangement of the derived benzoyl derivatives and subsequent hydrazinolysis of the resulting N-benzoylpyrroles.
Synthesis of sapphyrins via a '3+1+1' procedure
Shevchuk, Sergiy V.,Davis, Julian M.,Sessler, Jonathan L.
, p. 2447 - 2450 (2001)
Sapphyrins may be obtained in ca. 30% yield via the condensation of 1 equivalent of a tripyrrane dialdehyde with 2 equivalents of a β-substituted pyrrole, followed by oxidation with DDQ.
Regioselective substituent effects upon the synthesis of dipyrrins from 2-formyl pyrroles
Beh, Michael H.R.,Figliola, Carlotta,Lund, Kate-Lyn A.R.,Kajetanowicz, Aleksandra K.,Johnsen, Ann E.,Aronitz, Elise M.,Thompson, Alison
supporting information, p. 779 - 784 (2018/07/06)
The synthesis of symmetric α-free meso-H-dipyrrin hydrobromides from 5-H-2-formyl pyrroles was investigated. The self-condensation produces regioisomeric dipyrrins through adoption of two mechanistic pathways. The key difference between the two pathways lies in which position of the pyrrole directs nucleophilic attack. Through a systematic study involving various substituted and (or) isotopically labelled 5-H-2-formyl pyrroles, we herein provide evidence to suggest that not only do two mechanistic pathways exist, but the steric bulk of the substituent adjacent to the 5-unsubstituted position influences which pathway dominates.
Synthesis of 2,2′-bipyrrole-5-carboxaldehydes and their application in the synthesis of B-ring functionalized prodiginines and tambjamines
Kancharla, Papireddy,Reynolds, Kevin A.
, p. 8375 - 8385 (2013/09/02)
Facile, versatile, and cost-effective synthetic routes for the preparation of a range of new 3-alkyl-, 4-alkyl-, 3,4-dialkyl-, and 3-halo-4-alkyl-2, 2′-bipyrrole-5-carboxaldehydes have been developed. These 2,2′-bipyrrole-5-carboxaldehydes offer interesting potential as building blocks for making bioactive natural and unnatural products, as demonstrated by the synthesis of B-ring functionalized prodiginines (PGs) and tambjamines.
Compound and method of producing organic semiconductor device
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, (2011/04/26)
A method of producing an organic semiconductor device is provided in which a layer composed of an organic semiconductor having excellent crystallinity and orientation in a low-temperature region can be formed, and the device can be produced in the air. The method includes forming a layer composed of an organic semiconductor precursor on a base body and irradiating the organic semiconductor precursor with light, wherein the organic semiconductor precursor is a porphyrin compound or an azaporphyrin compound having in its molecule at least one of the structure represented by the following general formula (1) or (2):
Meso-unsubstituted iron corrole in hemoproteins: Remarkable differences in effects on peroxidase activities between myoglobin and horseradish peroxidase
Matsuo, Takashi,Hayashi, Akihiro,Abe, Masato,Matsuda, Takaaki,Hisaeda, Yoshio,Hayashi, Takashi
supporting information; experimental part, p. 15124 - 15125 (2010/01/30)
(Figure Presented) Myoglobin (Mb) and horseradish peroxidase (HRP) were both reconstituted with a meso-unsubstituted iron corrole and their electronic configurations and peroxidase activities were investigated. The appearance of the 540 nm band upon incorporation of the iron corrole into apoMb indicates axial coordination by the proximal histidine imidazole in the Mb heme pocket. Based on 1H NMR measurements using the Evans method, the total magnetic susceptibility of the iron corrole reconstituted Mb was evaluated to be S = 3/2. In contrast, although a band does not appear in the vicinity of 540 nm during reconstitution of the iron corrole into the matrix of HRP, a spectrum similar to that of the iron corrole reconstituted Mb is observed upon the addition of dithionite. This observation suggests that the oxidation state of the corrole iron in the reconstituted HRP can be assigned as +4. The catalytic activities of both proteins toward guaiacol oxidation are quite different; the iron corrole reconstituted HRP decelerates H2O2-dependent oxidation of guaiacol, while the same reaction catalyzed by iron corrole reconstituted Mb has the opposite effect and accelerates the reaction. This finding can be attributed to the difference in the oxidation states of the corrole iron when these proteins are in the resting state.
NOVEL COMPOUND AND METHOD OF PRODUCING ORGANIC SEMICONDUCTOR DEVICE
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, (2008/12/06)
A method of producing an organic semiconductor device is provided in which a layer composed of an organic semiconductor having excellent crystallinity and orientation in a low-temperature region can be formed, and the device can be produced in the air. The method includes forming a layer composed of an organic semiconductor precursor on a base body and irradiating the organic semiconductor precursor with light, wherein the organic semiconductor precursor is a porphyrin compound or an azaporphyrin compound having in its molecule at least one of the structure represented by the following general formula (1) or (2):
Microwave-assisted Piloty-Robinson synthesis of 3,4-disubstituted pyrroles
Milgram, Benjamin C.,Eskildsen, Katrine,Richter, Steven M.,Scheidt, W. Robert,Scheidt, Karl A.
, p. 3941 - 3944 (2008/02/01)
(Chemical Equation Presented) The synthesis of N-acyl 3,4-disubstituted pyrroles can be accomplished directly from hydrazine and an aldehyde via a Piloty-Robinson pyrrole synthesis. The use of microwave radiation for the cyclization and pyrrole formation
Intermolecularly hydrogen-bonded dimeric helices: tripyrrindiones
Roth, Steven D.,Shkindel, Tetyana,Lightner, David A.
, p. 11030 - 11039 (2008/02/12)
A rare and unusual class of tripyrrolic compounds, violet-colored tripyrrin-1,14-diones, can be prepared easily and in moderately high yields from base (piperidine)-catalyzed condensation of 3-pyrrolin-2-ones with 2,5-diformylpyrroles. Dipyrrinones adopt the all-syn-Z conformation leading to helical, lock-washer like structures, which form dimers that are held together by intermolecular hydrogen bonds in nonpolar solvents and in the crystal. Strong bathochromic spectral shifts of the tripyrrindione ～480 nm long wavelength UV-visible absorption band are seen with added base: DBU, 615 nm; TFA, 573 nm; and Zn(OAc)2, 586 nm.
Preparation of pyrrol and oxazole compounds; formation of porphyrins and C-acyl-α-amino acid esters therefrom
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, (2008/06/13)
A process for preparation of new or previously known pyrrol derivatives is provided. The process involves reacting a nitroalkane or a nitroalkene with an isocyanoacetate in the presence of a prophosphatrane "super base" to prepare the pyrrol compounds. Th
