124703-77-1Relevant articles and documents
Divergent Synthesis of Multisubstituted Unsymmetric Pyrroles and Pyrrolin-4-ones from Enamino Esters via Copper-Catalyzed Aerobic Dimerization
Chen, Zhi-Wei,Zheng, Lei,Liu, Jin
, p. 3051 - 3060 (2019)
A facile synthetic method to access multisubstituted unsymmetric pyrrole and pyrrolin-4-one derivatives is disclosed. In the presence of Cu(OAc)2 and KOAc, substituted pyrrole derivatives are produced in good yields (up to 93 %) through oxidative cyclization of enamino esters. Meanwhile, using CuCl2 and TFA (trifluoroacetic acid), pyrrolin-4-one derivatives are obtained in excellent yields (up to 94 %) through 1,2-aryl migration. A wide range of functional groups have been tolerated, and a reliable method for the synthesis of valuable multisubstituted pyrroles and pyrrolin-4-ones has been developed.
Cu-Mediated Expeditious Annulation of Alkyl 3-Aminoacrylates with Aryldiazonium Salts: Access to Alkyl N2-Aryl 1,2,3-Triazole-carboxylates for Druglike Molecular Synthesis
Liu, Hao-Nan,Cao, Hao-Qiang,Cheung, Chi Wai,Ma, Jun-An
, p. 1396 - 1401 (2020/02/22)
Alkyl N-aryl 1,2,3-triazole-carboxylates are important molecules or intermediates in medicinal chemistry, but the synthesis of N2-aryl counterparts remains elusive. Herein, we describe a Cu-mediated annulation reaction of alkyl 3-aminoacrylates with aryldiazonium salts, both of which are readily available substrates. Furthermore, alkyl 2-aminoacrylates are also viable substrates. Diverse alkyl N2-aryl 1,2,3-triazole-carboxylates and their analogues can be rapidly prepared under mild conditions. Especially, this protocol allows one to access several druglike variants of carbonic anhydrase inhibitors and celecoxib.
Facile entry to an efficient and practical enantioselective synthesis of a polycyclic cholesteryl ester transfer protein inhibitor
Han, Zhengxu S.,Xu, Yibo,Fandrick, Daniel R.,Rodriguez, Sonia,Li, Zhibin,Qu, Bo,Gonnella, Nina C.,Sanyal, Sanjit,Reeves, Jonathan T.,Ma, Shengli,Grinberg, Nelu,Haddad, Nizar,Krishnamurthy, Dhileep,Song, Jinhua J.,Yee, Nathan K.,Pfrengle, Waldemar,Ostermeier, Markus,Schnaubelt, Juergen,Leuter, Zeno,Steigmiller, Sonja,Daeubler, Juergen,Stehle, Emanuel,Neumann, Lukas,Trieselmann, Thomas,Tielmann, Patrick,Buba, Annette,Hamm, Rainer,Koch, Gunter,Renner, Svenja,Dehli, Juan R.,Schmelcher, Florian,Stange, Christian,MacK, Juergen,Soyka, Rainer,Senanayake, Chris H.
supporting information, p. 4142 - 4145 (2014/10/15)
An efficient enantioselective synthesis of the chiral polycyclic cholesteryl ester transfer protein (CETP) inhibitor 1 has been developed. The synthesis was rendered practical for large scale via the development of a modified Hantzsch-type reaction to prepare the sterically hindered pyridine ring, enantioselective hydrogenation of hindered ketone 6 utilizing novel BIBOP-amino-pyridine derived Ru complex, efficient ICl promoted lactone formation, and a BF3 mediated hydrogenation process for diastereoselective lactol reduction. This efficient route was successfully scaled to produce multikilogram quantities of challenging CETP drug candidate 1.