+ Translate

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

, : Regioselective cobalt-catalyzed formation of bicyclic 3- and 4-aminopyridines. Organic Letters 13(8): 2030-2033

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.

(PDF same-day service: $19.90)

Accession: 055445588

PMID: 21413688

DOI: 10.1021/ol200417p

Submit PDF Full Text: Here

Submit PDF Full Text

No spam - Every submission is manually reviewed

Due to poor quality, we do not accept files from Researchgate

Submitted PDF Full Texts will always be free for everyone
(We only charge for PDFs that we need to acquire)

Select a PDF file:

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...