54063-11-5Relevant articles and documents
Synthesis and properties of 5,6-dihydrodipyrrolo[1,2-d;2′,1′-g] [1,4]diazepin-11-one
Johnston, Karen A.,McNab, Hamish
, p. 1703 - 1708 (2009)
Treatment of 1,2-di(pyrrol-1-yl)ethane 4 with oxalyl chloride gave a low yield of 5,6-dihydrodipyrrolo[1,2-d;2′,1′-g][1,4]diazepin-11-one 2, by an unexpected electrophilic substitution-decarbonylation process. The diazepinone 2 is unreactive to electrophiles, but can be deoxygenated to 5,6-dihydro-11H-dipyrrolo[1,2-d;2′,1′-g][1,4]diazepine 9 with lithium aluminium hydride. Reaction of 1,1-di(pyrrol-1-yl)methane 5 with triphosgene gives the related dipyrrolo[1,2-c;2′,1′-f]pyrimidin-10- one 3. NMR spectroscopic and X-ray crystal structure comparisons of 2 and 3 show that there is unexpectedly greater conjugation in the compound with the core seven-membered ring, 2, even though the molecule as a whole is less planar than 3. The corresponding reactions of 4 or 5 with thiophosgene did not give cyclisation products but the O-methyl thioesters 7 and 8 were obtained (89 and 27%, respectively).
Markovnikov-selective palladium catalyst for carbonylation of alkynes with heteroarenes
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Paragraph 0014; 0015, (2019/01/24)
The invention relates to a Markovnikov-selective palladium catalyst for carbonylation of alkynes with heteroarenes. In particular, the invention relates to a compound having the structure (1).
Markovnikov-Selective Palladium Catalyst for Carbonylation of Alkynes with Heteroarenes
Liu, Jie,Li, Haoquan,Dühren, Ricarda,Liu, Jiawang,Spannenberg, Anke,Franke, Robert,Jackstell, Ralf,Beller, Matthias
supporting information, p. 11976 - 11980 (2017/09/06)
A new class of palladium catalysts, based on heterocyclic diphosphines, was rationally designed and synthesized. Application of one of these catalysts allows novel Markovnikov-selective carbonylation of non-activated alkynes with heteroarenes to give the
EFFICIENT SYNTHESIS OF 1,1'-METHYLENEBIS-1H-PYRROLE DERIVATIVES
Gonzalez, Carlos R.,Greenhouse, Robert
, p. 1127 - 1130 (2007/10/02)
The title compounds may be prepared efficiently by the reaction of methylene chloride with the pyrrolyl anion generated under phase-transfer conditions.The spectral characteristics of these relatively unknown compounds are discussed.
REACTIONS OF NITROGEN CONTAINING AROMATIC ANIONS WITH CHLOROCARBENE
Burger, U.,Dreier, F.
, p. 2065 - 2072 (2007/10/02)
It is shown that the 4-azapentalene anion (1) and the dipyrroloimidazolyl anion (2) (Li salts) undergo eliminative ring fission upon reaction with chlorocarbene in tetrahydrofuran.Acetylenes (12 and 18) are the result.The reaction of 1 is accompanied by ring enlargement to indolizine (7).When the reaction of 1 with chlorocarbene is performed in diethylether, again 7 is produced, this time accompanied by a tetracyclic valence isomer, the pyrroloazabenzvalene (8).Mechanistic implications, based on the finding that the site of label incorporation in the enlarged products is solvent dependent, are discussed and compared with the corresponding reactions of carboaromatic anions.Use of intramolecular oxidative coupling for the synthesis of new pyrrolo annellated heterocyclic systems is made throughout this work.
On the Use of N,N'-Dipyrrolylmethane in Heterocyclic Synthesis. Dipyrrol-2H-imidazole and its Aromatic Anion
Burger, Ulrich,Dreier, Francine
, p. 1190 - 1197 (2007/10/02)
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.
