+ Site Statistics
+ Search Articles
+ Subscribe to Site Feeds
EurekaMag Most Shared ContentMost Shared
EurekaMag PDF Full Text ContentPDF Full Text
+ PDF Full Text
Request PDF Full TextRequest PDF Full Text
+ Follow Us
Follow on FacebookFollow on Facebook
Follow on TwitterFollow on Twitter
Follow on Google+Follow on Google+
Follow on LinkedInFollow on LinkedIn

+ Translate

Regioselective cobalt-catalyzed formation of bicyclic 3- and 4-aminopyridines

Organic Letters 13(8): 2030-2033

Regioselective cobalt-catalyzed formation of bicyclic 3- and 4-aminopyridines

Bimolecular cobalt-catalyzed [2 + 2 + 2] cycloadditions between yne-ynamides and nitriles afford bicyclic 3- or 4-aminopyridines in up to 100% yield. The high regioselectivity observed depends on the substitution pattern at the starting ynamide. Aminopyridines bearing TMS and Ts groups are efficiently deprotected in an orthogonal fashion.

Accession: 055445588

PMID: 21413688

DOI: 10.1021/ol200417p

Related references

Spahn, N.A.; Nguyen, M.H.; Renner, J.; Lane, T.K.; Louie, J., 2016: Regioselective Iron-Catalyzed [2 + 2 + 2] Cycloaddition Reaction Forming 4,6-Disubstituted 2-Aminopyridines from Terminal Alkynes and Cyanamides. NlmCategory="UNASSIGNED">Iron complexes bound by redox-active pyridine dialdimine (PDAI) ligands catalyze the cycloaddition of two terminal alkynes and one cyanamide. The reaction is both chemo- and regioselective, as only 4,6-disubst...

Parnell C.A.; Vollhardt K.P.C., 1985: The cobalt way to vitamin b 6 regioselective construction of the tetra substituted pyridine nucleus by cobalt catalyzed alkyne nitrile cooligomerizations. Cocyclization of bis(trimethylsilyl)- and bis(trimethylstannyl(di-2-propynyl ether with acetonitrile provides a synthetic entry into 1,3-dihydro-6-methyl-4,7-bis(trimethylsilyl)- and bis(trimethylstannyl)-furo[3,4-c]pyridines. Regioselective elect...

Liu, C-Che.; Korivi, R.Prasad.; Cheng, C-Hong., 2008: Cobalt-catalyzed regioselective synthesis of indenamine from o-iodobenzaldimine and alkyne: intriguing difference to the nickel-catalyzed reaction. Chemistry 14(31): 9503-9506

Garcia, P.; Evanno, Y.; George, P.; Sevrin, M.; Ricci, G.; Malacria, M.; Aubert, C.; Gandon, V., 2012: Synthesis of aminopyridines and aminopyridones by cobalt-catalyzed [2+2+2] cycloadditions involving yne-ynamides: scope, limitations, and mechanistic insights. An in-depth study of the cobalt-catalyzed [2+2+2] cycloaddition between yne-ynamides and nitriles to afford aminopyridines has been carried out. About 30 nitriles exhibiting a broad range of steric demand and electronic properties have been evalua...

Kubota, M.; Saito, T.; Miyamoto, K.; Hirano, K.; Wang, C.; Uchiyama, M., 2016: Gold-Catalyzed Cyclization of Alkyne Alcohols: Regioselective Construction of Functionalized 6,6- and 6,7-Bicyclic Ethers. We describe an efficient regioselective formation of six-/seven-membered cyclic ethers based on gold-catalyzed intramolecular hydroalkoxylation. Sequential gold-catalyzed cyclization and palladium-catalyzed cross-coupling reactions afforded 6,6-bi...

Lane, T.K.; D'Souza, B.R.; Louie, J., 2013: Iron-catalyzed formation of 2-aminopyridines from diynes and cyanamides. Diynes and cyanamides undergo an iron-catalyzed [2 + 2 + 2] cycloaddition to form highly substituted 2-aminopyridines in an atom-efficient manner that is both high yielding and regioselective. This system was also used to cyclize two terminal alky...

Langer; Saleh, 2000: Regioselective synthesis of medium-sized bicyclic butenolides by lewis acid catalyzed cyclization of cyclic 1, 3-Bis(trimethylsilyloxy)-1,3-butadienes with oxalyl chloride. A new strategy for the synthesis of medium-sized bicyclic gamma-alkylidenebutenolides is reported which involves Me(3)SiOTf-catalyzed cyclization of cyclic 1, 3-bis(trimethylsilyloxy)-1,3-butadienes with oxalyl chloride.

Girijavallabhan, V.; Alvarez, C.; Njoroge, F.George., 2012: Regioselective cobalt-catalyzed addition of sulfides to unactivated alkenes. A novel method to synthesize tertiary alkyl/aryl sulfides in a mild and regioselective manner from unactivated alkenes using cobalt catalysis is described. The methodology is compatible with sensitive functionalities and is successful with several...

Schmidt, A.; Hilt, G., 2013: Scope and limitations of 1,3,5-hexatriene derivatives in regioselective cobalt-catalyzed reactions. Applications of 1,3,5-hexatriene derivatives in atom-economic cobalt-catalyzed transformations, such as the Diels-Alder reaction with alkynes, the 1,4-hydrovinylation reaction with terminal alkenes, and the 1,4-hydrohexatrienylation reaction, are...

Kobayashi, T.; Ohmiya, H.; Yorimitsu, H.; Oshima, K., 2008: Cobalt-catalyzed regioselective dehydrohalogenation of alkyl halides with dimethylphenylsilylmethylmagnesium chloride. Cobalt-catalyzed reactions of haloalkanes with dimethylphenylsilylmethylmagnesium chloride result in highly regioselective dehydrohalogenation. The reaction does not follow the conventional E2 elimination mechanism but includes beta-hydride elimin...