102619-05-6Relevant articles and documents
Iron-Catalyzed Synthesis of C2 Aryl- and N-Heteroaryl-Substituted Tetrahydropyrans
Bosset, Cyril,Angibaud, Patrick,Stanfield, Ian,Meerpoel, Lieven,Berthelot, Didier,Guérinot, Amandine,Cossy, Janine
, p. 12509 - 12525 (2015)
An iron-catalyzed cyclization of hydroxy allylic derivatives into tetrahydropyrans possessing an N-heteroaryl at C2 is disclosed. The reaction proceeds with good yield and in high diastereoselectivity in favor of the more stable isomer. The diastereoselectivity results from an iron-induced reopening of the tetrahydropyrans, allowing a thermodynamic equilibration. The method allows access to a variety of 2,6-disubstituted as well as 2,4,6-trisubstituted tetrahydropyrans that could be considered as attractive scaffolds for the pharmaceutical industry.
Gold catalysis: Phenol synthesis in the presence of functional groups
Hashmi, A. Stephen K.,Weyrauch, Jan P.,Kurpejovic, Elzen,Frost, Tanja M.,Miehlich, Burkhard,Frey, Wolfgang,Bats, Jan W.
, p. 5806 - 5814 (2006)
The effect of different substituants, such as bromo, chloromethyl, hydroxymethyl, formyl, acetyl, carboxy, and acylated hydroxymethyl and ammonium groups, on the furan ring of substrates in gold-catalyzed phenol synthesis has been investigated. The furan
Discovery of Azaindole Ureas as a Novel Class of Bacterial Gyrase B Inhibitors
Zhang, Jing,Yang, Qingyi,Cross, Jason B.,Romero, Jan Antoinette C.,Poutsiaka, Katherine M.,Epie, Felix,Bevan, Douglas,Wang, Bin,Zhang, Yanzhi,Chavan, Ajit,Zhang, Xin,Moy, Terence,Daniel, Anu,Nguyen, Kien,Chamberlain, Brian,Carter, Nicole,Shotwell, Joseph,Silverman, Jared,Metcalf, Chester A.,Ryan, Dominic,Lippa, Blaise,Dolle, Roland E.
, p. 8503 - 8512 (2015)
The emergence and spread of multidrug resistant bacteria are widely believed to endanger human health. New drug targets and lead compounds exempt from cross-resistance with existing drugs are urgently needed. We report on the discovery of azaindole ureas as a novel class of bacterial gyrase B inhibitors and detail the story of their evolution from a de novo design hit based on structure-based drug design. These inhibitors show potent minimum inhibitory concentrations against fluoroquinolone resistant MRSA and other Gram-positive bacteria.
Pd-catalyzed allylative dearomatisation using Grignard reagents
Boldrini, Cosimo,Harutyunyan, Syuzanna R.
supporting information, p. 11807 - 11810 (2021/11/30)
Pd-catalyzed allylative dearomatisation of naphthyl halides is shown to be feasible by employing Grignard reagents. The high reactivity of the nucleophile allows for fast reactions and low catalyst loading, while a plethora of successfully substituted compounds illustrate the broad scope. Five membered heteroaromatic compounds are also demonstrated to be reactive under similar conditions.
Serendipitous base catalysed condensation-heteroannulation of iminoesters: a regioselective route to the synthesis of 4,6-disubstituted 5-azaindoles
Chelvam, Venkatesh,Dudhe, Premansh,Pathak, Biswarup,Venkatasubbaiah, Krishnan
supporting information, p. 1582 - 1587 (2020/03/06)
A serendipitous discovery of a novel one-pot synthesis of 4,6-disubstituted 5-azaindoles is reported herein. In the presence of Hunig's base, various N-substituted pyrrole-2-carboxaldehydes have been efficiently transformed into their corresponding 4,6-disubstituted 5-azaindoles through an imine mediated cascade condensation-heteroannulation. The synthetic value of the methodology is established by preparing a novel chemical analogue of a cannabinoid receptor type 2 (CB2) agonist.
Proton-exchanged montmorillonite-mediated reactions of hetero-benzyl acetates: Application to the synthesis of Zafirlukast
Yang, Lei,Chen, Xuan,Ni, Kaidong,Li, Yuansheng,Wu, Jianhong,Chen, Weilin,Ji, Yin,Feng, Lili,Li, Fei,Chen, Dongyin
supporting information, (2020/06/28)
Proton-exchanged montmorillonite (H-mont) with outstanding surface characteristics can provide abundant acidic sites in the mesopores, and serve as an efficient heterogeneous catalyst for the synthesis of heterocycle-containing diarylmethanes via Friedel-Crafts-like alkylation of (hetero)arenes by heterobenzyl acetates under mild reaction conditions without requiring any additives or an inert atmosphere. Using this strategy, the gram-scale synthesis of indole-containing diarylmethane 13 has been accomplished in good yield for the preparation of Zafirlukast. In addition, H-mont can be applied to the nucleophilic substitution reactions of heterobenzyl acetate 5p with a variety of alcohols and 1,3-dicarbonyl compounds.
