The Experts below are selected from a list of 2181 Experts worldwide ranked by ideXlab platform
Renzo Rossi - One of the best experts on this subject based on the ideXlab platform.
-
An Economical Access to 3,4‐Diaryl‐2(5H)‐furanones and 4‐Aryl‐6‐methyl‐2(2H)‐Pyranones by Pd‐Catalyzed Suzuki‐Type Arylation of 3‐Aryl‐4‐tosyloxy‐2(5H)‐furanones and 6‐Methyl‐4‐tosyloxy‐2(2H)‐Pyranones, Respectively
European Journal of Organic Chemistry, 2009Co-Authors: Fabio Bellina, Chiara Marchetti, Renzo RossiAbstract:Both symmetrical and unsymmetrical 3,4-diaryl-substituted 2(5H)-furanones have been efficiently synthesized using an inexpensive procedure involving the Pd(OAc)2/PCy3-catalyzed Suzuki-type arylation of readily available 3-aryl-4-tosyloxy-2(5H)-furanones as the key step. The mild conditions of this arylation protocol have also been used for the high yielding synthesis of 4-aryl-6-methyl-2(2H)-Pyranones from 6-methyl-4-tosyloxy-2(2H)-Pyranone. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)
-
6-Chloro-2(2H)-Pyranone: a new 2(2H)-Pyranone synthon
Tetrahedron Letters, 2003Co-Authors: Matteo Biagetti, Adriano Carpita, Fabio Bellina, Renzo RossiAbstract:6-Chloro-2(2H)-Pyranone, which can be prepared in high yield from commercially available trans-glutaconic acid, undergoes facile Pd/Cu-catalyzed reaction with various 1-alkynes to give rise to the corresponding 6-(1-alkynyl)-2(2H)-Pyranones in moderate to good yields. These last hitherto unknown compounds have been used as direct precursors to 6-alkyl- and 6-[(Z)-1-alkenyl]-2(2H)-Pyranones.
-
New procedures for the selective synthesis of 2(2H)-Pyranone derivatives and 3-aryl-4-iodoisocoumarins
Tetrahedron, 2002Co-Authors: Matteo Biagetti, Adriano Carpita, Paolo Stabile, Fabio Bellina, Renzo RossiAbstract:Abstract 5-Iodo-2(2 H )-Pyranone derivatives have been selectively synthesized by reaction of stereodefined methyl 2-en-4-ynoates with iodine in MeCN, CH 2 Cl 2 or C 6 H 6 at 20°C (Method C) or by treatment of these esters with ICl in CH 2 Cl 2 at 20°C (Method B). Methods B and C proved also to be suitable for the preparation of 3-aryl-4-iodoisocoumarins from the corresponding methyl 2-(arylethynyl)benzoates. Interestingly, the high selectivity of iodolactonization of stereodefined methyl 2-en-4-ynoates by Method B allowed preparation in moderate yields of 2(2 H )-Pyranone derivatives by a one-pot sequence of iodolactonization and Stille-type reactions.
-
Selective Synthesis of 5,6‐Disubstituted 3‐Methyl‐2(2H)‐Pyranones and 6‐Substituted 3‐Methyl‐2(2H)‐Pyranones, Including Fusalanipyrone and Gibepyrone A
European Journal of Organic Chemistry, 2002Co-Authors: Matteo Biagetti, Adriano Carpita, Fabio Bellina, Stéphane Viel, Luisa Mannina, Renzo RossiAbstract:The 6-substituted 3-bromo-5-iodo-2(2H)-Pyranones 11, prepared by iodolactonization of the corresponding 5-substituted (E)-2-bromo-2-en-4-ynoic acids 10, were used as precursors to 5,6-disubstituted 3-methyl-2(2H)-Pyranones 8 and 6-substituted 3-methyl-2(2H)-Pyranones 7. The synthesis of compounds 8 involved two consecutive Stille-type reactions, whereas the approach followed to prepare compounds 7 consisted of the selective reduction of the dihalogen derivatives 11 to the corresponding 6-substituted 3-bromo-2(2H)-Pyranones 12, followed by a Pd/Cu-catalysed reaction with tetramethyltin. However, this synthetic approach to compounds 7 proved to be unsuitable for preparing stereoisomerically pure fusalanipyrone (7a), a natural product isolated from Fusarium solani. Nevertheless, 7a and gibepyrone A (7b), which is a natural product isolated from Gibberella fujikuroi, could be synthesized in stereoisomerically pure form by reaction sequences involving iodolactonization of easily available (2Z,6Z)- and (2Z,6E)-2,6-dimethyl-2,6-octadien-4-ynoic acids (16a) and (16b), respectively, followed by Pd-catalysed triethylammonium formate reduction of the thus obtained 6-substituted 5-iodo-3-methyl-2(2H)-Pyranones 17a and 17b, respectively. (© Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002)
-
selective synthesis of natural and unnatural 5 6 disubstituted 2 2h Pyranones via iodolactonization of 5 substituted z 2 en 4 ynoic acids
Tetrahedron, 2001Co-Authors: Fabio Bellina, Adriano Carpita, Matteo Biagetti, Renzo RossiAbstract:Abstract Reaction of 5-substituted ( Z )-2-en-4-ynoic acids with iodine and NaHCO 3 in CH 3 CN or with ICl in CH 2 Cl 2 affords mixtures of ( E )-5-(1-iodoylidene)-2(5 H )-furanones and 6-substituted 5-iodo-2(2 H )-Pyranones in which these last compounds are the major products. The 5-iodo-2(2 H )-Pyranones, which are easily separated chromatographically from the corresponding regioisomers, are able to undergo Stille-type reactions with a variety of organotin compounds to give 5,6-disubstituted 2(2 H )-Pyranones in moderate to good yields. One of these compounds, i.e. 5-(1-butynyl)-2(2 H )-Pyranone, has been used as direct precursor to two substances produced by fungal culture LL-11G219, which function as androgen ligands, i.e. ( Z )-5-(1-butenyl)-6-methyl-2(2 H )-Pyranone and 5-butyl-6-methyl-2(2 H )-Pyranone.
Fabio Bellina - One of the best experts on this subject based on the ideXlab platform.
-
An Economical Access to 3,4‐Diaryl‐2(5H)‐furanones and 4‐Aryl‐6‐methyl‐2(2H)‐Pyranones by Pd‐Catalyzed Suzuki‐Type Arylation of 3‐Aryl‐4‐tosyloxy‐2(5H)‐furanones and 6‐Methyl‐4‐tosyloxy‐2(2H)‐Pyranones, Respectively
European Journal of Organic Chemistry, 2009Co-Authors: Fabio Bellina, Chiara Marchetti, Renzo RossiAbstract:Both symmetrical and unsymmetrical 3,4-diaryl-substituted 2(5H)-furanones have been efficiently synthesized using an inexpensive procedure involving the Pd(OAc)2/PCy3-catalyzed Suzuki-type arylation of readily available 3-aryl-4-tosyloxy-2(5H)-furanones as the key step. The mild conditions of this arylation protocol have also been used for the high yielding synthesis of 4-aryl-6-methyl-2(2H)-Pyranones from 6-methyl-4-tosyloxy-2(2H)-Pyranone. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)
-
6-Chloro-2(2H)-Pyranone: a new 2(2H)-Pyranone synthon
Tetrahedron Letters, 2003Co-Authors: Matteo Biagetti, Adriano Carpita, Fabio Bellina, Renzo RossiAbstract:6-Chloro-2(2H)-Pyranone, which can be prepared in high yield from commercially available trans-glutaconic acid, undergoes facile Pd/Cu-catalyzed reaction with various 1-alkynes to give rise to the corresponding 6-(1-alkynyl)-2(2H)-Pyranones in moderate to good yields. These last hitherto unknown compounds have been used as direct precursors to 6-alkyl- and 6-[(Z)-1-alkenyl]-2(2H)-Pyranones.
-
New procedures for the selective synthesis of 2(2H)-Pyranone derivatives and 3-aryl-4-iodoisocoumarins
Tetrahedron, 2002Co-Authors: Matteo Biagetti, Adriano Carpita, Paolo Stabile, Fabio Bellina, Renzo RossiAbstract:Abstract 5-Iodo-2(2 H )-Pyranone derivatives have been selectively synthesized by reaction of stereodefined methyl 2-en-4-ynoates with iodine in MeCN, CH 2 Cl 2 or C 6 H 6 at 20°C (Method C) or by treatment of these esters with ICl in CH 2 Cl 2 at 20°C (Method B). Methods B and C proved also to be suitable for the preparation of 3-aryl-4-iodoisocoumarins from the corresponding methyl 2-(arylethynyl)benzoates. Interestingly, the high selectivity of iodolactonization of stereodefined methyl 2-en-4-ynoates by Method B allowed preparation in moderate yields of 2(2 H )-Pyranone derivatives by a one-pot sequence of iodolactonization and Stille-type reactions.
-
Selective Synthesis of 5,6‐Disubstituted 3‐Methyl‐2(2H)‐Pyranones and 6‐Substituted 3‐Methyl‐2(2H)‐Pyranones, Including Fusalanipyrone and Gibepyrone A
European Journal of Organic Chemistry, 2002Co-Authors: Matteo Biagetti, Adriano Carpita, Fabio Bellina, Stéphane Viel, Luisa Mannina, Renzo RossiAbstract:The 6-substituted 3-bromo-5-iodo-2(2H)-Pyranones 11, prepared by iodolactonization of the corresponding 5-substituted (E)-2-bromo-2-en-4-ynoic acids 10, were used as precursors to 5,6-disubstituted 3-methyl-2(2H)-Pyranones 8 and 6-substituted 3-methyl-2(2H)-Pyranones 7. The synthesis of compounds 8 involved two consecutive Stille-type reactions, whereas the approach followed to prepare compounds 7 consisted of the selective reduction of the dihalogen derivatives 11 to the corresponding 6-substituted 3-bromo-2(2H)-Pyranones 12, followed by a Pd/Cu-catalysed reaction with tetramethyltin. However, this synthetic approach to compounds 7 proved to be unsuitable for preparing stereoisomerically pure fusalanipyrone (7a), a natural product isolated from Fusarium solani. Nevertheless, 7a and gibepyrone A (7b), which is a natural product isolated from Gibberella fujikuroi, could be synthesized in stereoisomerically pure form by reaction sequences involving iodolactonization of easily available (2Z,6Z)- and (2Z,6E)-2,6-dimethyl-2,6-octadien-4-ynoic acids (16a) and (16b), respectively, followed by Pd-catalysed triethylammonium formate reduction of the thus obtained 6-substituted 5-iodo-3-methyl-2(2H)-Pyranones 17a and 17b, respectively. (© Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002)
-
selective synthesis of natural and unnatural 5 6 disubstituted 2 2h Pyranones via iodolactonization of 5 substituted z 2 en 4 ynoic acids
Tetrahedron, 2001Co-Authors: Fabio Bellina, Adriano Carpita, Matteo Biagetti, Renzo RossiAbstract:Abstract Reaction of 5-substituted ( Z )-2-en-4-ynoic acids with iodine and NaHCO 3 in CH 3 CN or with ICl in CH 2 Cl 2 affords mixtures of ( E )-5-(1-iodoylidene)-2(5 H )-furanones and 6-substituted 5-iodo-2(2 H )-Pyranones in which these last compounds are the major products. The 5-iodo-2(2 H )-Pyranones, which are easily separated chromatographically from the corresponding regioisomers, are able to undergo Stille-type reactions with a variety of organotin compounds to give 5,6-disubstituted 2(2 H )-Pyranones in moderate to good yields. One of these compounds, i.e. 5-(1-butynyl)-2(2 H )-Pyranone, has been used as direct precursor to two substances produced by fungal culture LL-11G219, which function as androgen ligands, i.e. ( Z )-5-(1-butenyl)-6-methyl-2(2 H )-Pyranone and 5-butyl-6-methyl-2(2 H )-Pyranone.
Atul Goel - One of the best experts on this subject based on the ideXlab platform.
-
Synthesis of Solution-Processable Donor-Acceptor Pyranone Dyads for White Organic Light-Emitting Devices.
The Journal of organic chemistry, 2019Co-Authors: Chandra P. Sharma, Neeraj M. Gupta, Jagriti Singh, Rohit Ashok Kumar Yadav, Deepak Kumar Dubey, Kundan S. Rawat, Ajay K. Jha, Jwo-huei Jou, Atul GoelAbstract:A series of donor–acceptor Pyranones (3a–m, 4a–h) were synthesized using α-oxo-ketene-S,S-acetal as the synthon for their application as emissive materials for energy-saving organic light-emitting devices (OLEDs). Among them, five Pyranones 3f, 3g, 3h, 3m, and 4e exhibited highly bright fluorescence in the solid state and weak or no emission in the solution state. Photophysical analysis of these dyes revealed that only 3f and 3m showed aggregation-induced emission behavior in a THF/water mixture (0–99%) with varying water fractions (fw) leading to bright fluorescence covering the entire visible region, while other derivatives 3g, 3h, and 4e did not show any fluorescence signal. The computational studies of the compounds revealed that the longer wavelength absorption originates from HOMO to LUMO electronic excitation. These dyes exhibited good thermal stability with 5% weight loss temperature in the range of 218–347 °C. The potential application of the donor–acceptor Pyranone dyads was demonstrated by fabr...
-
synthesis of solution processable donor acceptor Pyranone dyads for white organic light emitting devices
Journal of Organic Chemistry, 2019Co-Authors: Chandra P. Sharma, Neeraj M. Gupta, Jagriti Singh, Rohit Ashok Kumar Yadav, Deepak Kumar Dubey, Kundan S. Rawat, Ajay K. Jha, Jwo-huei Jou, Atul GoelAbstract:A series of donor-acceptor Pyranones (3a-m, 4a-h) were synthesized using α-oxo-ketene- S, S-acetal as the synthon for their application as emissive materials for energy-saving organic light-emitting devices (OLEDs). Among them, five Pyranones 3f, 3g, 3h, 3m, and 4e exhibited highly bright fluorescence in the solid state and weak or no emission in the solution state. Photophysical analysis of these dyes revealed that only 3f and 3m showed aggregation-induced emission behavior in a THF/water mixture (0-99%) with varying water fractions ( fw) leading to bright fluorescence covering the entire visible region, while other derivatives 3g, 3h, and 4e did not show any fluorescence signal. The computational studies of the compounds revealed that the longer wavelength absorption originates from HOMO to LUMO electronic excitation. These dyes exhibited good thermal stability with 5% weight loss temperature in the range of 218-347 °C. The potential application of the donor-acceptor Pyranone dyads was demonstrated by fabrication of solution-processed OLEDs. Remarkably, OLED devices prepared using highly emissive compounds 6-(anthracen-9-yl)-4-(methylthio)-2-oxo-2 H-pyran-3-carbonitrile (3m) and 6-(4-methoxyphenyl)-4-(methylthio)-2-oxo-2 H-pyran-3-carbonitrile (3f) displayed pure white emission with CIE coordinates of (0.29, 0.31) and (0.32, 0.32), respectively. Additionally, the resultant devices exhibited external quantum efficiencies of 1.9 and 1.2% at 100 cd m-2, respectively.
Matteo Biagetti - One of the best experts on this subject based on the ideXlab platform.
-
6-Chloro-2(2H)-Pyranone: a new 2(2H)-Pyranone synthon
Tetrahedron Letters, 2003Co-Authors: Matteo Biagetti, Adriano Carpita, Fabio Bellina, Renzo RossiAbstract:6-Chloro-2(2H)-Pyranone, which can be prepared in high yield from commercially available trans-glutaconic acid, undergoes facile Pd/Cu-catalyzed reaction with various 1-alkynes to give rise to the corresponding 6-(1-alkynyl)-2(2H)-Pyranones in moderate to good yields. These last hitherto unknown compounds have been used as direct precursors to 6-alkyl- and 6-[(Z)-1-alkenyl]-2(2H)-Pyranones.
-
New procedures for the selective synthesis of 2(2H)-Pyranone derivatives and 3-aryl-4-iodoisocoumarins
Tetrahedron, 2002Co-Authors: Matteo Biagetti, Adriano Carpita, Paolo Stabile, Fabio Bellina, Renzo RossiAbstract:Abstract 5-Iodo-2(2 H )-Pyranone derivatives have been selectively synthesized by reaction of stereodefined methyl 2-en-4-ynoates with iodine in MeCN, CH 2 Cl 2 or C 6 H 6 at 20°C (Method C) or by treatment of these esters with ICl in CH 2 Cl 2 at 20°C (Method B). Methods B and C proved also to be suitable for the preparation of 3-aryl-4-iodoisocoumarins from the corresponding methyl 2-(arylethynyl)benzoates. Interestingly, the high selectivity of iodolactonization of stereodefined methyl 2-en-4-ynoates by Method B allowed preparation in moderate yields of 2(2 H )-Pyranone derivatives by a one-pot sequence of iodolactonization and Stille-type reactions.
-
Selective Synthesis of 5,6‐Disubstituted 3‐Methyl‐2(2H)‐Pyranones and 6‐Substituted 3‐Methyl‐2(2H)‐Pyranones, Including Fusalanipyrone and Gibepyrone A
European Journal of Organic Chemistry, 2002Co-Authors: Matteo Biagetti, Adriano Carpita, Fabio Bellina, Stéphane Viel, Luisa Mannina, Renzo RossiAbstract:The 6-substituted 3-bromo-5-iodo-2(2H)-Pyranones 11, prepared by iodolactonization of the corresponding 5-substituted (E)-2-bromo-2-en-4-ynoic acids 10, were used as precursors to 5,6-disubstituted 3-methyl-2(2H)-Pyranones 8 and 6-substituted 3-methyl-2(2H)-Pyranones 7. The synthesis of compounds 8 involved two consecutive Stille-type reactions, whereas the approach followed to prepare compounds 7 consisted of the selective reduction of the dihalogen derivatives 11 to the corresponding 6-substituted 3-bromo-2(2H)-Pyranones 12, followed by a Pd/Cu-catalysed reaction with tetramethyltin. However, this synthetic approach to compounds 7 proved to be unsuitable for preparing stereoisomerically pure fusalanipyrone (7a), a natural product isolated from Fusarium solani. Nevertheless, 7a and gibepyrone A (7b), which is a natural product isolated from Gibberella fujikuroi, could be synthesized in stereoisomerically pure form by reaction sequences involving iodolactonization of easily available (2Z,6Z)- and (2Z,6E)-2,6-dimethyl-2,6-octadien-4-ynoic acids (16a) and (16b), respectively, followed by Pd-catalysed triethylammonium formate reduction of the thus obtained 6-substituted 5-iodo-3-methyl-2(2H)-Pyranones 17a and 17b, respectively. (© Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002)
-
selective synthesis of natural and unnatural 5 6 disubstituted 2 2h Pyranones via iodolactonization of 5 substituted z 2 en 4 ynoic acids
Tetrahedron, 2001Co-Authors: Fabio Bellina, Adriano Carpita, Matteo Biagetti, Renzo RossiAbstract:Abstract Reaction of 5-substituted ( Z )-2-en-4-ynoic acids with iodine and NaHCO 3 in CH 3 CN or with ICl in CH 2 Cl 2 affords mixtures of ( E )-5-(1-iodoylidene)-2(5 H )-furanones and 6-substituted 5-iodo-2(2 H )-Pyranones in which these last compounds are the major products. The 5-iodo-2(2 H )-Pyranones, which are easily separated chromatographically from the corresponding regioisomers, are able to undergo Stille-type reactions with a variety of organotin compounds to give 5,6-disubstituted 2(2 H )-Pyranones in moderate to good yields. One of these compounds, i.e. 5-(1-butynyl)-2(2 H )-Pyranone, has been used as direct precursor to two substances produced by fungal culture LL-11G219, which function as androgen ligands, i.e. ( Z )-5-(1-butenyl)-6-methyl-2(2 H )-Pyranone and 5-butyl-6-methyl-2(2 H )-Pyranone.
-
Selective synthesis of natural and unnatural 5,6-disubstituted 2(2H)-Pyranones via iodolactonization of 5-substituted (Z)-2-en-4-ynoic acids
Tetrahedron, 2001Co-Authors: Fabio Bellina, Adriano Carpita, Matteo Biagetti, Renzo RossiAbstract:Abstract Reaction of 5-substituted ( Z )-2-en-4-ynoic acids with iodine and NaHCO 3 in CH 3 CN or with ICl in CH 2 Cl 2 affords mixtures of ( E )-5-(1-iodoylidene)-2(5 H )-furanones and 6-substituted 5-iodo-2(2 H )-Pyranones in which these last compounds are the major products. The 5-iodo-2(2 H )-Pyranones, which are easily separated chromatographically from the corresponding regioisomers, are able to undergo Stille-type reactions with a variety of organotin compounds to give 5,6-disubstituted 2(2 H )-Pyranones in moderate to good yields. One of these compounds, i.e. 5-(1-butynyl)-2(2 H )-Pyranone, has been used as direct precursor to two substances produced by fungal culture LL-11G219, which function as androgen ligands, i.e. ( Z )-5-(1-butenyl)-6-methyl-2(2 H )-Pyranone and 5-butyl-6-methyl-2(2 H )-Pyranone.
Kundan S. Rawat - One of the best experts on this subject based on the ideXlab platform.
-
Synthesis of Solution-Processable Donor-Acceptor Pyranone Dyads for White Organic Light-Emitting Devices.
The Journal of organic chemistry, 2019Co-Authors: Chandra P. Sharma, Neeraj M. Gupta, Jagriti Singh, Rohit Ashok Kumar Yadav, Deepak Kumar Dubey, Kundan S. Rawat, Ajay K. Jha, Jwo-huei Jou, Atul GoelAbstract:A series of donor–acceptor Pyranones (3a–m, 4a–h) were synthesized using α-oxo-ketene-S,S-acetal as the synthon for their application as emissive materials for energy-saving organic light-emitting devices (OLEDs). Among them, five Pyranones 3f, 3g, 3h, 3m, and 4e exhibited highly bright fluorescence in the solid state and weak or no emission in the solution state. Photophysical analysis of these dyes revealed that only 3f and 3m showed aggregation-induced emission behavior in a THF/water mixture (0–99%) with varying water fractions (fw) leading to bright fluorescence covering the entire visible region, while other derivatives 3g, 3h, and 4e did not show any fluorescence signal. The computational studies of the compounds revealed that the longer wavelength absorption originates from HOMO to LUMO electronic excitation. These dyes exhibited good thermal stability with 5% weight loss temperature in the range of 218–347 °C. The potential application of the donor–acceptor Pyranone dyads was demonstrated by fabr...
-
synthesis of solution processable donor acceptor Pyranone dyads for white organic light emitting devices
Journal of Organic Chemistry, 2019Co-Authors: Chandra P. Sharma, Neeraj M. Gupta, Jagriti Singh, Rohit Ashok Kumar Yadav, Deepak Kumar Dubey, Kundan S. Rawat, Ajay K. Jha, Jwo-huei Jou, Atul GoelAbstract:A series of donor-acceptor Pyranones (3a-m, 4a-h) were synthesized using α-oxo-ketene- S, S-acetal as the synthon for their application as emissive materials for energy-saving organic light-emitting devices (OLEDs). Among them, five Pyranones 3f, 3g, 3h, 3m, and 4e exhibited highly bright fluorescence in the solid state and weak or no emission in the solution state. Photophysical analysis of these dyes revealed that only 3f and 3m showed aggregation-induced emission behavior in a THF/water mixture (0-99%) with varying water fractions ( fw) leading to bright fluorescence covering the entire visible region, while other derivatives 3g, 3h, and 4e did not show any fluorescence signal. The computational studies of the compounds revealed that the longer wavelength absorption originates from HOMO to LUMO electronic excitation. These dyes exhibited good thermal stability with 5% weight loss temperature in the range of 218-347 °C. The potential application of the donor-acceptor Pyranone dyads was demonstrated by fabrication of solution-processed OLEDs. Remarkably, OLED devices prepared using highly emissive compounds 6-(anthracen-9-yl)-4-(methylthio)-2-oxo-2 H-pyran-3-carbonitrile (3m) and 6-(4-methoxyphenyl)-4-(methylthio)-2-oxo-2 H-pyran-3-carbonitrile (3f) displayed pure white emission with CIE coordinates of (0.29, 0.31) and (0.32, 0.32), respectively. Additionally, the resultant devices exhibited external quantum efficiencies of 1.9 and 1.2% at 100 cd m-2, respectively.
