- K2S2O8mediated synthesis of 5-Aryldipyrromethanes and meso-substituted A4-Tetraarylporphyrins
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The synthesis of dipyrromethanes from pyrrole and arylglyoxylic acids in the presence of K2S2O8at 90 C is reported affording dipyrromethanes in very good yields. Unlike an excess pyrrole traditionally used in dipyrromethane synthesis, the current method uses a stoichiometric amount of pyrrole avoiding any use of Br?nsted or Lewis acid. A gram scale synthesis of 5-phenyldipyrromethane is also achieved demonstrating potential scale up of dipyrromethanes using this method feasible. Subsequently, dipyrromethanes were converted to A4tetraarylporphyrins also in the presence of K2S2O8at 90C. A direct synthesis of A4-tetraphenylporphyrin from excess pyrrole and phenylglyoxylic acid in the presence of K2S2O8 at 90C is also reported.
- Laha, Joydev K.,Hunjan, Mandeep Kaur
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p. 664 - 673
(2021/06/03)
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- Synthesis and Band Gap Analysis of Designed Porphyrin Derivatives Containing Electron Donating and Accepting Group
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Symmetric (DD, AA1–AA5) and non-symmetric (DA1) porphyrin derivatives were synthesized through McDonald coupling of bispyrrole 2D, 2A1–2A5 with the corresponding aldehyde 3 or diol 6 as a key step. The UV–Vis spectrum and CV of those porphyrins were measu
- Chang, In-Jung,Jeon, Yea-Sel,Hwang, Kwang-Jin
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p. 173 - 179
(2019/02/14)
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- Synthesis of dipyroromethanes in water and investigation of electronic and steric effects in efficiency of olefin epoxidation by sodium periodate catalyzed by manganese tetraaryl and trans disubstituted porphyrin complexes
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Condensation of pyrrole with various aldehydes in the presence of BF3?etherate as an acid catalyst in water provides good yield of some dipyrromethanes. Prolongation of the reaction time with aldehydes substituted by electron-donating (mesityl) or electron-withdrawing (2,6-dichlorophenyl) groups on the ortho positions of the phenyl did not lead to decomposition or scrambling. Manganese trans disubstituted porphyrin complexes which derive from various dipyrromethanes and manganese tetraaryl porphyrin complexes including various substituents with different steric and electronic properties show good catalytic activity in epoxidation of alkenes by NaIO4 in the presence of imidazole (ImH). The study of steric and electronic effects of the catalysts on the epoxidation of olefins shows that Mn-porphyrin complexes with more bulky and electron-releasing groups on meso phenyls could increase the epoxidation yield of most alkenes.
- Bagherzadeh, Mojtaba,Jonaghani, Mohammad Adineh,Amini, Mojtaba,Mortazavi-Manesh, Anahita
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p. 671 - 678
(2019/04/26)
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- Green synthesis of dipyrromethanes in aqueous media catalyzed by SO3H-functionalized ionic liquid
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A mild, efficient and metal-free method was described for the green synthesis of dipyrromethanes from aldehydes and unsubstituted pyrrole catalyzed by SO3H-functionalized ionic liquids (SO3H-ILs) in aqueous media at room temperature. Notably, SO3H-ILs, 1-butylsulfonic-3-methylimidazolium hydrogen sulfate ([bsmim][HSO4]) was the most efficient catalyst for moderate to good yields of the corresponding desired products.
- Senapak,Saeeng,Jaratjaroonphong,Kasemsuk,Sirion
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p. 1302 - 1310
(2016/02/03)
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- An easily accessible and recyclable copper nanoparticle catalyst for the solvent-free synthesis of dipyrromethanes and aromatic amines
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A facile method to prepare a reusable copper nanocatalyst is reported. Transmission electron microscopy shows that the CuNPs are spherical in nature and reside in the nanoscopic template of the capping agent, guar gum. Powder X-ray diffraction studies confirm the crystalline nature of the CuNPs. The catalytic efficiency and recyclability of the synthesized CuNPs were demonstrated through the synthesis of dipyrromethanes (DPMs) and aromatic amines. Various DPMs are obtained in very good yields under solvent-free conditions and nitroarenes are converted to the corresponding amino compounds within 10 min, as evidenced by the kinetic study.
- Megarajan, Sengan,Ayaz Ahmed, Khan Behlol,Rajmohan, Rajamani,Vairaprakash, Pothiappan,Anbazhagan, Veerappan
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p. 103065 - 103071
(2016/11/13)
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- Synthesis of dipyrromethanes in aqueous media using boric acid
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Boric acid acts as an efficient and green catalyst for the condensation reaction of pyrrole and aldehydes in aqueous medium to produce parallel library of dipyrromethanes including new compound analogue, meso-acetyldipyrromethane in moderate to good yield. The use of boric acid as catalyst and selective reactivity of aldehydes over ketones in its presence, and water as reaction medium are important attributes in the present protocol.
- Singhal, Anchal,Singh, Snigdha,Chauhan, Shive M. S.
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p. 144 - 151
(2018/05/09)
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- Synthesis and catalytic properties of trans-A2B2-type metalloporphyrins in cyclohexane oxidation
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A new efficient and mild protocol for synthesizing a series of trans-A 2B2-porphyrins through a TFA-catalyzed condensation reaction between various aldehydes and dipyrromethanes has been developed. Several trans-A2B2-metalloporphyrins (cobalt, nickel) were synthesized and used to catalyze cyclohexane oxidation C-H bonds with dioxygen in the absence of additives and solvents. The results show that the catalytic activities were relative to the nature of the substituted groups and the central metal ions of trans-A2B2-metalloporphyrin. Cobalt metalloporphyrin presents better catalytic performance in the conversion of cyclohexane than the nickel metalloporphyrin under the same reaction conditions.
- Xie, Yujia,Zhang, Fengyong,Liu, Pingle,Hao, Fang,Luo, He'An
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- Synthesis and evaluation of gold(III) complexes as efficient DNA binders and cytotoxic agents
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In recent years, great interest has been focused on gold(III) complexes as cytotoxic and antitumor drugs. Recent studies demonstrated that simple bidentate or polydentate ligands containing nitrogen donor atoms may offer sufficient redox stabilization to produce viable Au(III) anticancer drug targets under physiologic conditions. So, we have synthesized square planer Au(III) complexes of type [Au(An)Clx]Cly and characterized them using UV-Vis absorption, C, H, N elemental analysis, FT-IR, LC-MS, 1H and 13C NMR spectroscopy. These compounds manifested significant cytotoxic properties in vitro for brine shrimp lethality bioassay. The metal complexes were screened for series of DNA binding activity using UV-Vis absorption titration, hydrodynamic measurement and thermal DNA denaturation study. The nucleolytic activity was performed on plasmid pUC19 DNA. The Michaelis-Menten kinetic studies were performed to evaluate rate of enhancement in metal complexes mediated DNA cleavage over the non-catalyzed DNA cleavage.
- Patel, Mohan N.,Bhatt, Bhupesh S.,Dosi, Promise A.
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- New copper complex derivatives including bis-dipyrrinato ligand for color filter pigments
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Four red compounds for color filter (CF) pigments in which phenyl, 4-chloro-phenyl, 4-fluoro-phenyl and pentafluorophenyl groups are substituted to 5-position of dipyrrinato group based on bis-dipyrrinato ligand were synthesized, and physical properties f
- Park, Jongwook,Park, Junghyo,Shin, Hawnkyu,Park, Youngil,Shin, Yunseop,Kim, Seungho
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scheme or table
p. 43 - 49
(2012/10/18)
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- Unique versatility of Amberlyst 15. An acid and solvent-free paradigm towards synthesis of bis(heterocyclyl)methane derivatives
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Bis(heterocyclyl)methanes, key intermediates for a variety of chemical, biochemical and material science relevant targets, have been obtained in a synthetically useful manner using Amberlyst 15 ion-exchange resin. This method promises versatility, cost-ef
- Singh, Kamaljit,Sharma, Shivali,Sharma, Amit
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scheme or table
p. 34 - 37
(2011/10/17)
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- α-/β-formylated boron-dipyrrin (BODIPY) dyes: Regioselective syntheses and photophysical properties
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Formylation has been performed on pyrrole-unsubstituted dipyrromethanes 1 and boron-dipyrrin (BODIPY) dyes 4 based on a Vilsmeier-Haack reaction. It is highly regioselective and complementary and occurs exclusively at the α-and β-position, respectively, f
- Yu, Changjiang,Jiao, Lijuan,Yin, Hao,Zhou, Jinyuan,Pang, Weidong,Wu, Yangchun,Wang, Zhaoyun,Yang, Gaosheng,Hao, Erhong
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body text
p. 5460 - 5468
(2011/11/29)
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- An eco-friendly procedure for the efficient synthesis of bis(indolyl)methanes in aqueous media
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A new, convenient and high yielding procedure for the preparation of bis(indolyl)methanes in water by electrophilic substitution reaction of indoles with different carbonyl compounds in the presence of a catalytic amount of [Cu(3,4-tmtppa)](MeSO4/su
- Sobhani, Sara,Safaei, Elham,Hasaninejad, Ali-Reza,Rezazadeh, Soodabeh
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experimental part
p. 3027 - 3031
(2009/12/01)
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- A novel method for the synthesis of dipyrromethanes by metal triflate catalysis
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5-Substituted dipyrromethanes were synthesized by the reaction of N-tosyl imines with excess pyrrole in the presence of metal triflates. Tripyrromethane and other oligomeric side products were not observed. High yields of 5-substituted dipyrromethanes wer
- Temelli, Baris,Unaleroglu, Canan
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p. 10130 - 10135
(2007/10/03)
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- Hexamethylenetetraamine-bromine catalyzed rapid and efficient synthesis of bis(indolyl)methanes
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Highly rapid and convenient syntheses of bis(indolyl)methanes in excellent yields were carried out using the inexpensive and easily available catalyst, hexamethylenetetraamine-bromine (HMTAB). Mild reaction conditions, short reaction times, and excellent yields are important features of this method. Springer-Verlag 2004.
- Bandgar, Babasaheb P.,Bettigeri, Sampada V.,Joshi, Neeta S.
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p. 1265 - 1273
(2007/10/03)
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- Facile synthesis of meso-substituted dipyrromethanes and porphyrins using cation exchange resins
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The macroporosity and acidity of cation exchange resins play a crucial role in the synthesis of dipyrromethanes and porphyrins; for the first time, cation exchange resins have been used as heterogeneous solid acid catalysts to produce dipyrromethanes and porphyrins in good yields. The reaction, at room temperature, of substituted aromatic aldehydes with pyrrole catalysed by cation exchange resin afforded the corresponding meso-substituted dipyrromethane in yields ranging from 70 to 80%, indicating the broad scope of the reaction. Further, the condensation of meso-substituted dipyrromethane with similar or different substituted aromatic aldehydes, using cation exchange resins furnished meso-tetrakis-symmetrical and mixed porphyrins, respectively. One-pot synthesis of porphyrins can also be carried out directly from the aldehydes and pyrrole under the above conditions. Acidolysis of the dipyrromethane is negligible under the conditions of the porphyrin-forming reaction.
- Naik, Rajan,Joshi, Padmakar,Kaiwar, Sharada P.,Deshpande, Rajesh K.
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p. 2207 - 2213
(2007/10/03)
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- Synthesis of novel porphyrin-based biscalix[4]arenes
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A novel method for the preparation of porphyrin-based biscalix[4]arenes has been developed, starting from appropriate aryldipyrrolyhnethane and calix[4]arene monoaldehyde. The condensation reaction in the presence of BF3 · Et2O leads
- Dudic, Miroslav,Lhotak, Pavel,Kral, Vladimir,Lang, Kamil,Stibor, Ivan
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p. 5949 - 5952
(2007/10/03)
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- Direct synthesis of aryldipyrromethanes
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The synthesis of aryldipyrromethanes from the direct condensation of pyrroles with aromatic aldehydes is described. Yields are improved with strong electronegative substituents on the aromatic aldehyde.
- Vigmond, Stephen J.,Chang, Martin C.,Kallury, Krishna M. R.,Thompson, Michael
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p. 2455 - 2458
(2007/10/02)
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