3274-54-2Relevant academic research and scientific papers
A HYDROFORMYLATION ROUTE TO Β-SUBSTITUTED PYRROLES
Campi, Eva M.,Jackson, W. Roy,Nilsson, Ylva
, p. 1093 - 1094 (1991)
Rhodium catalysed hydroformylation of readily available β-alkynylamines gives 3-substituted or 2,4-disubstituted pyrroles in good yields.
Ratiometric Fluorescence Acid Probes Based on a Tetrad Structure including a Single BODIPY Chromophore
Zhou, Zheyang,Maki, Toshihide
, p. 17560 - 17566 (2021/10/25)
A series of tetrad BODIPY derivatives were synthesized. Each molecule was shown to contain phenyl groups at the 1- and 7-positions and a pyridyl or quinolyl group at the 8-position of the BODIPY chromophore. They exhibited fluorescence shifts in the presence of acids. These results imply the importance of controlled conjugation as well as shielding of the meso-substituent from solvents to achieve fluorescence shifts and efficiency through a tetrad structure including a single boron dipyrromethenes (BODIPY) chromophore.
Efficient Far-Red/Near-IR Absorbing BODIPY Photocages by Blocking Unproductive Conical Intersections
Shrestha, Pradeep,Dissanayake, Komadhie C.,Gehrmann, Elizabeth J.,Wijesooriya, Chamari S.,Mukhopadhyay, Atreyee,Smith, Emily A.,Winter, Arthur H.
supporting information, p. 15505 - 15512 (2020/10/20)
Photocages are light-sensitive chemical protecting groups that give investigators control over activation of biomolecules using targeted light irradiation. A compelling application of far-red/near-IR absorbing photocages is their potential for deep tissue activation of biomolecules and phototherapeutics. Toward this goal, we recently reported BODIPY photocages that absorb near-IR light. However, these photocages have reduced photorelease efficiencies compared to shorter-wavelength absorbing photocages, which has hindered their application. Because photochemistry is a zero-sum competition of rates, improvement of the quantum yield of a photoreaction can be achieved either by making the desired photoreaction more efficient or by hobbling competitive decay channels. This latter strategy of inhibiting unproductive decay channels was pursued to improve the release efficiency of long-wavelength absorbing BODIPY photocages by synthesizing structures that block access to unproductive singlet internal conversion conical intersections, which have recently been located for simple BODIPY structures from excited state dynamic simulations. This strategy led to the synthesis of new conformationally restrained boron-methylated BODIPY photocages that absorb light strongly around 700 nm. In the best case, a photocage was identified with an extinction coefficient of 124000 M-1 cm-1, a quantum yield of photorelease of 3.8%, and an overall quantum efficiency of 4650 M-1 cm-1 at 680 nm. This derivative has a quantum efficiency that is 50-fold higher than the best known BODIPY photocages absorbing >600 nm, validating the effectiveness of a strategy for designing efficient photoreactions by thwarting competitive excited state decay channels. Furthermore, 1,7-diaryl substitutions were found to improve the quantum yields of photorelease by excited state participation and blocking ion pair recombination by internal nucleophilic trapping. No cellular toxicity (trypan blue exclusion) was observed at 20 μM, and photoactivation was demonstrated in HeLa cells using red light.
Pyrrole derivative as well as preparation method and application thereof
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, (2020/09/12)
The invention belongs to the field of medical chemistry, and relates to a pyrrole derivativex as well as a preparation method and application thereof. A compound with a structure shown as a general formula (I), or one or a mixture of more of a tautomer, a
Rhodium-catalyzed transannulation of 1,2,3-triazoles to polysubstituted pyrroles
Rajasekar, Shanmugam,Anbarasan, Pazhamalai
, p. 8428 - 8434 (2015/03/18)
Rhodium-catalyzed transannulation of N-sulfonyl-1,2,3-triazoles with vinyl ether has been accomplished for the synthesis of various polysubstituted pyrroles. The present method allows the synthesis of mono-, di-, and trisubstituted pyrroles with appropriate substitutions. Furthermore, the developed methodology was applied in the formal synthesis of neolamellarin A, an antitumor agent.
Simple two-step synthesis of 2,4-disubstituted pyrroles and 3,5-disubstituted pyrrole-2-carbonitriles from enones
Kucukdisli, Murat,Ferenc, Dorota,Heinz, Marcel,Wiebe, Christine,Opatz, Till
, p. 466 - 470 (2014/03/21)
The cyclocondensation of enones with aminoacetonitrile furnishes 3,4-dihydro-2H-pyrrole-2-carbonitriles which can be readily converted to 2,4-disubstituted pyrroles by microwave-induced dehydrocyanation. Alternatively, oxidation of the intermediates produ
3-Methyl-4-phenylpyrrole from the ants Anochetus kempfi and Anochetus mayri
Jones,Flournoy,Torres,Snelling,Spande,Garraffo
, p. 1343 - 1345 (2007/10/03)
The cephalic extracts of the ant Anochetus kempfi were found to contain 2,5-dimethyl-3-isoamylpyrazine (1) and 3-methyl-4-phenylpyrrole (2). The structures of these compounds were established from their spectral data and by comparison with synthetic samples. This is the first report of a phenylpyrrole found in an insect and only the third report of a pyrrole from ants.
Rhodium-Catalysed Reactions of Propargylamines with CO/H2. Formation of Pyrroles and Butenolides
Campi, Eva M.,Fallon, Gary D.,Jackson, W. Roy,Nilsson, Ylva
, p. 1167 - 1178 (2007/10/02)
Rhodium-catalysed reactions of (arylpropargyl)amines with CO/H2 give β-arylpyrroles in good yields.Reactions of (alkylpropargyl)amines gave alkylpyrroles together with butenolides which are formed in an unusual reaction that probably involves double carbonylation, reduction of one carbonyl function and removal of the amine function by hydrogenolysis.The single-crystal X-ray structure of 5-methyl-N,3-diphenylpyrrole-2-carboxamide is recorded.
