61034-86-4Relevant articles and documents
Bronsted Acid Catalyzed Cyclization of Inert N-Substituted Pyrroles to Benzo[ f ]pyrrolo[1,2- a ][1,4]diazepines
Gao, Zeng,Qian, Jinlong,Yang, Huameng,Zhang, Jinlong,Jiang, Gaoxi
, p. 930 - 934 (2021/04/27)
Two approaches involving intramolecular and intermolecular cyclization, respectively, have been developed for the direct and practical construction of a series of important benzo[ f ]pyrrolo[1,2- a ][1,4]azepines by using Bronsted acid catalysts. Upon catalysis by TsOH, the intramolecular dehydroxylation/ring closure of 3-hydroxy-2-[2-(1 H -pyrrol-1-yl)benzyl]isoindolin-1-ones provided various racemic benzo[ f ]pyrrolo[1,2- a ][1,4]azepines in high yields. Furthermore, enantioenriched benzo[ f ]pyrrolo[1,2- a ][1,4]azepines were also obtained by chiral phosphoric acid catalyzed intermolecular addition of [2-(1 H -pyrrol-1-yl)phenyl]methanamines to 2-formylbenzoates under mild conditions.
Regioselective synthesis of diversely substituted diazoninones through a post-Ugi gold-catalyzed intramolecular hydroarylation process
Li, Zhenghua,Kumar, Amit,Vachhani, Dipak D.,Sharma, Sunil K.,Parmar, Virinder S.,Van Der Eycken, Erik V.
supporting information, p. 2084 - 2091 (2014/04/17)
A highly efficient approach for the regioselective construction of fused nine-membered rings (diazoninone framework) was developed by employing sequential Ugi and gold-catalyzed intramolecular hydroarylation reactions. The scope of this intramolecular cyc
Reactions of 2-(pyrrol-1-yl)benzyl radicals and related species under flash vacuum pyrolysis conditions
Cadogan,Clark, Bernard A. J.,Ford, Daniel,MacDonald, Ranald J.,MacPherson, Andrew D.,McNab, Hamish,Nicolson, Iain S.,Reed, David,Sommerville, Craig C.
supporting information; experimental part, p. 5173 - 5183 (2010/04/03)
2-(Pyrrol-1-yl)phenoxyl, aminyl, thiophenoxyl and benzyl radicals 2a-2d, respectively, were generated in the gas-phase under flash vacuum pyrolysis conditions. In all cases except the phenoxyl, cyclisation took place providing acceptable synthetic routes to the fused heterocycles 11, 14 and 15, respectively. Only sigmatropic rearrangement products were isolated, in low yields, from the phenoxyl 2a. The pyrrolo[1,2-a]benzimidazole 11 adopts the 1H-tautomer exclusively in chloroform solution. Electrophilic substitution reactions of pyrrolo[2,1-b]benzothiophene 14 were studied, including protonation, deuterium exchange, Vilsmeier formylation and reaction with dimethyl acetylenedicarboxylate. 2-(2,5-Diarylpyrrol-1-yl)thiophenoxyl, phenoxyl and aminyl radicals 23a-f, were also generated in the gas-phase under similar conditions. The thiophenoxyls 23a/b gave extremely complex pyrolysate mixtures in which primary cyclisation products were formed by attack of the radical at the pyrrrole ring and attack at the ipso-, ortho- and meta- positions of the aryl ring. Secondary pyrolysis products were obtained by specific sigmatropic shifts of the N-aryl group. The 2,5-di(thien-2-yl)thiophenoxyl radical 23c gave the pyrrolobenzothiazole 31c as the only cyclisation product in low yield. FVP of the phenoxyl and aminyl radical generators 26d and 26f, respectively, gave 3-arylpyrrolo[1,2-f]phenanthridines 46d and 46f, respectively, by a hydrogen transfer-cyclisation mechanism.