10087-64-6Relevant articles and documents
Synthesis of pyrrolo-pyrrolo-pyrazines via the Pd/C-catalyzed cyclization of N-propargyl pyrrolinyl-pyrrole derivatives
Aslanoglu, Furgan,Basceken, Sinan,Balci, Metin
, p. 449 - 451 (2019)
A novel and efficient synthesis of N-substituted dipyrrolo[1,2-a:2′,1′-c]pyrazine derivatives has been developed. The synthetic strategy relies on the synthesis of 4′,5′-dihydro-1H,3′H-2,2′-bipyrrole, followed by the reaction with propargyl bromide. Various substituents were introduced to the alkyne functionality using the Sonogashira coupling reaction. Aromatization of the dihydropyrrole ring followed by an intramolecular cyclization reaction between the alkyne functionality and the pyrrole nitrogen atom was catalyzed by Pd/C at high temperature to furnish the desired dipyrrolo-pyrazine skeleton.
Regioselective bipyrrole coupling of pyrroles and 3-substituted pyrroles using phenyliodine(III) bis(trifluoroacetate)
Dohi, Toshifumi,Morimoto, Koji,Ito, Motoki,Kita, Yasuyuki
, p. 2913 - 2919 (2007)
A series of electron-rich bipyrroles were prepared by the regioselective, phenyliodine(III) bis(trifluoroacetate) (PIFA) induced oxidative coupling of pyrroles in the presence of bromotrimethylsilane. Using pyrrole and 3,4-disubstituted pyrroles gave exclusively 2,2′-linked bipyrroles without the formation of other bipyrrole regioisomers. The 3-alkyl- or 3-aryl-substituted pyrroles gave unsymmetrical H-T dimers in high yields as the major isolable α-linked bipyrrole products over the symmetrical H-H dimers. The nature of the N-substituent significantly influences the regioselectivity of the reaction, thus regiocontrolled bipyrrole coupling of N-phenyl- and N-benzyl-substituted pyrroles gave 2,3′-bipyrroles. Georg Thieme Verlag Stuttgart.
On the Use of N,N'-Dipyrrolylmethane in Heterocyclic Synthesis. Dipyrrol-2H-imidazole and its Aromatic Anion
Burger, Ulrich,Dreier, Francine
, p. 1190 - 1197 (1980)
The pyrrolate ion (5) is shown to produce N, N'-dipyrrolyl methane (4) when reacted with dichloromethane under conditions of weak counter-ion association. 1-Azoniafulvene ion (13) is sggested to be the key intermediate in this reaction.N,N'-dipyrrolyl methane (4) undergoes intramolecular oxidative coupling when treated with butyllithium and Cu(II)chloride, yielding the novel ring system of dipyrrolo-2H-imidazole (3).The latter upon reaction with methyl lithium forms the Hueckel-aromatic anion 2.Solutions of the lithium salt are stable for several days.Reaction of the dianion of 2,2'-bipyrrole (11) with dichloromethane doesi40 not produce 3, but a pyrrolophane-type dimer (12) having its two anticoplanar N,N'-bipyrrolediyl subunits arranged in a double layer and joined by a methylene group on each side.
The long and winding road to new porphycenes
Czerski, Igor,Listkowski, Arkadiusz,Nawrocki, Jan,Urbańska, Natalia,Piwoński, Hubert,Soko?owski, Adam,Pietraszkiewicz, Oksana,Pietraszkiewicz, Marek,Waluk, Jacek
, p. 589 - 602 (2012)
We describe attempts - not always successful - made over the years to improve the efficiency of porphycene synthesis and to produce novel compounds, custom-designed for specific purposes. New porphycenes are reported, some of them obtained rather unexpectedly as by-products of the planned reactions. Structure and energy computations of possible tautomeric forms in porphycenes substituted by one, two, three, and four tert-butyl groups lead to predictions regarding the kinetics and mechanisms of intramolecular double hydrogen transfer. The occurrence of tautomerization in single molecules of tert-butylsubstituted porphycenes is demonstrated by using fluorescence polarization techniques.
Synthesis of a meso-Tetraalkylporphycene Bearing Reactive Sites: Toward Porphycene–Polydimethylsiloxane Hybrids with Enhanced Photophysical Properties
Ono, Toshikazu,Shinjo, Hyuga,Koga, Daiki,Hisaeda, Yoshio
, p. 7578 - 7583 (2019/12/03)
meso-Tetraalkyl porphycenes exhibit unique optical properties with wide potential applications. The very fact that incorporation of porphycenes into polymeric materials is rare, make this approach a particularly attractive one. In this work, meso-tetrakis
