- Bronsted Acid Catalyzed Cyclization of Inert N-Substituted Pyrroles to Benzo[ f ]pyrrolo[1,2- a ][1,4]diazepines
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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.
- Gao, Zeng,Qian, Jinlong,Yang, Huameng,Zhang, Jinlong,Jiang, Gaoxi
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p. 930 - 934
(2021/04/27)
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- Regioselective synthesis of diversely substituted diazoninones through a post-Ugi gold-catalyzed intramolecular hydroarylation process
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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
- Li, Zhenghua,Kumar, Amit,Vachhani, Dipak D.,Sharma, Sunil K.,Parmar, Virinder S.,Van Der Eycken, Erik V.
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supporting information
p. 2084 - 2091
(2014/04/17)
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- Intramolecular redox reaction for the synthesis of N-aryl pyrroles catalyzed by Lewis acids
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An efficient approach to synthesize N-aryl pyrroles via Lewis acid-mediated 1,5-hydride shift and isomerization of 2-(3-pyrroline-1-yl)arylaldehydes has been achieved in up to 89% yield. This methodology is applicable to the synthesis of fluorazene deriva
- Du, Hong-Jin,Zhen, Le,Wen, Xiaoan,Xu, Qing-Long,Sun, Hongbin
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p. 9716 - 9719
(2015/02/19)
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- Efficient synthesis of 9H-pyrrolo[1,2-a]indol-9-one derivatives based on active manganese dioxide promoted intramolecular cyclization
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A series of 9H-pyrrolo[1,2-a]indol-9-ones have been prepared via in-situ sequential oxidation of [2-(1H-pyrrol-1-yl)phenyl]methanols promoted by active manganese dioxide. The procedure led to title compounds in good yields under mild conditions, without the need to isolate the intermediate aldehydes.
- Aiello, Francesca,Garofalo, Antonio,Grande, Fedora
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experimental part
p. 274 - 277
(2010/03/01)
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- Reactions of 2-(pyrrol-1-yl)benzyl radicals and related species under flash vacuum pyrolysis conditions
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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.
- Cadogan,Clark, Bernard A. J.,Ford, Daniel,MacDonald, Ranald J.,MacPherson, Andrew D.,McNab, Hamish,Nicolson, Iain S.,Reed, David,Sommerville, Craig C.
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supporting information; experimental part
p. 5173 - 5183
(2010/04/03)
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- Morita-Baylis-Hillman route to 4H-pyrrolo[1,2-a][1]benzazepine derivatives
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A simple method for synthesizing substituted 4H-pyrrolo[1,2-a][1]benzazepines using acid-assisted cyclization of the Morita-Baylis-Hillman adducts of 2-(1H-pyrrol-1-yl)benzaldehydes with methyl acrylate or methyl vinyl ketone as a key step has been developed.
- Park, Sun Pil,Song, Young Seok,Lee, Kee-Jung
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experimental part
p. 4703 - 4708
(2009/10/02)
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- Synthesis of condensed pyrroloindoles via Pd-catalyzed intramolecular C-H bond functionalization of pyrroles
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A new strategy for the synthesis of condensed hetero- or carbocycles such as pyrroloindoles or fluorenes has been developed that involves the Pd-catalyzed cyclization of readily available N-(2-halobenzyl)pyrroles or their phenyl derivatives. The reaction is proposed to proceed via oxidative addition of benzylic halides to Pd(0) followed by base-assisted C-H bond activation. A broad range of condensed cyclic products could be obtained in good to excellent yields under mild conditions. Copyright
- Seung, Jun Hwang,Seung, Hwan Cho,Chang, Sukbok
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supporting information; experimental part
p. 16158 - 16159
(2009/05/08)
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- Biaryl-methanethio-, -sulphinyl- and sulphonyl derivatives
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The present invention is related to chemical compositions, processes for the preparation thereof and uses of the composition. Particularly, the present invention relates to compositions that include substituted biaryl-methanesulfinyl acetamides of Formula
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Page/Page column 64-65
(2008/06/13)
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- Lewis acid catalyzed synthesis of 4-aminopyrrolo[1,2-a]quinolin-5-ol derivatives from 2-(1-pyrrolyl)benzaldehyde and isocyanides
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Reaction of 2-(1-pyrrolyl)benzaldehyde with isocyanides in the presence of a catalytic amount of boron trifluoride diethyl etherate was followed by treatment with acetic anhydride in pyridine to give the corresponding O-acetyl derivatives of 4-alkyl(or ar
- Kobayashi, Kazuhiro,Nakahashi, Ryoji,Takanohashi, Atsushi,Kitamura, Taichi,Morikawa, Osamu,Konishi, Hisatoshi
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p. 624 - 625
(2007/10/03)
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- Polycondensed heterocycles. Part 11: Preparation and regioselective reductions of 5-phenyl-4H-pyrrolo[1,2-α][1]benzazepin-4-one
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The Wadsworth-Emmons olefination between 2-(1H-pyrrol-1-yl)benzaldehyde and methyl α-(diethylphosphonyl)phenyl-acetate leads exclusively to the cis-isomer of methyl 2-(1H-pyrrol-1-yl)-α-phenylcinnamate, which, after transformation into the corresponding a
- Garofalo, Antonio,Ragno, Gaetano,Campiani, Giuseppe,Brizzi, Antonella,Nacci, Vito
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p. 9351 - 9355
(2007/10/03)
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- 2-[(2-Aminobenzyl)sulfinyl]-1-(2-pyridyl)-1,4,5,6- tetrahydrocyclopent[d]imidazoles as a novel class of gastric H+/K+-ATPase inhibitors
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Substituted 2-sulfinylimidazoles were synthesized and investigated as potential inhibitors of gastric H+/K+-ATPase. The 4,5-unsubstituted imidazole series 6-11 and the 1,4,5,6-tetrahydrocyclopent[d]imidazole series 12 were found to be potent inhibitors of the acid secretory enzyme H+/K+- ATPase. Structure-activity relationships indicate that the substitution of 2- pyridyl groups at the 1-position of the imidazole moiety combined with (2- aminobenzyl)sulfinyl groups at the 2-position leads to highly active compounds with a favorable chemical stability. Other substitution patterns in the imidazole moiety result in reducing biological activities. 2-[(2- Aminobenzyl)sulfinyl]-1-[2-(3-methylpyridyl)]-1,4,5,6- tetrahydrocyclopent[d]imidazole (12h, T-776) was selected for further development as a potential clinical candidate. Extensive study on the acid degradation of 12h indicates a mechanism of action different from that of omeprazole, the first H+/K+-ATPase inhibitor introduced to the market.
- Yamada,Yura,Morimoto,Harada,Yamada,Honma,Kinoshita,Sugiura
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p. 596 - 604
(2007/10/03)
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- Pyridyl-substituted imidazoles, compositions containing same and methods of use thereof
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Novel imidazole of the formula: STR1 wherein Ring A is pyridyl group or a substituted pyridyl group; Ring B is phenyl group or a substituted phenyl group; R1 and R2 are hydrogen atom or are combined together to form a group of the formula: --(CH2)q --; m is 1 or 2; n is 0, 1 or 2; and q is 3 or 4, or a salt thereof are disclosed. Said derivative (I) and a salt thereof are useful as anti-ulcer agents.
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- Pyrrolo[1,2-a] [4,1]benzoxazepine derivatives useful as calmodulin and histamine inhibitors
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Disclosed are the compounds of the formula STR1 wherein n represents the integer 1,2,3 or 4; R1 represents hydrogen, lower alkyl, halogen, trifluoromethyl, hydroxy or lower alkoxy; R2 represents hydrogen or lower alkyl; R3
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