Concepedia

Highly Regioselective DABCO‐Catalyzed Nucleophilic Aromatic Substitution (S<sub>N</sub>Ar) Reaction of Methyl 2,6‐Dichloronicotinate with Phenols

Yao‐Jun Shi, Guy R. Humphrey, Peter E. Maligres, Robert A. Reamer, J. Michael Williams

Advanced Synthesis & Catalysis · 2006 · 44 citations · 9 references

DOI

Concepts

Abstract

Abstract Exclusive formation of 6‐aryloxy ethers 9 from an S N Ar reaction of methyl 2,6‐dichloronicotinate ( 2 ) with phenols 7 catalyzed by 1,4‐diazabicyclo[2.2.2]octane (DABCO) in the presence of stoichiometric triethylamine is described. The reaction proceeds via the regioselective formation of an unprecedented DABCO‐pyridine adduct 10a .

References

9

Dual Nucleophilic Catalysis with DABCO for the N-Methylation of Indoles

Wen‐Chung Shieh, Steven Dell, Andrew Bach et al. · The Journal of Organic Chemistry · 2003 · 87 citations

, , +17

Efficient Synthesis of 2-Aryl-6-chloronicotinamides via PXPd2-Catalyzed Regioselective Suzuki Coupling

Wu Yang, Yufeng Wang, James R. Corte · Organic Letters · 2003 · 66 citations

, , +13

The use of the 2,4‐dinitrophenyl group in sugar chemistry re‐examined

H. J. Koeners, A. J. de Kok, C. Romers et al. · Recueil des Travaux Chimiques des Pays-Bas · 1980 · 44 citations

, , +13

Synthesis and Structure−Affinity Relationships of Novel<i>N</i>-(1-Ethyl-4-methylhexahydro-1,4-diazepin-6-yl)pyridine-3-carboxamides with Potent Serotonin 5-HT<sub>3</sub>and Dopamine D<sub>2</sub>Receptor Antagonistic Activity

Yoshimi Hirokawa, Iwao Fujiwara, Kenji Suzuki et al. · Journal of Medicinal Chemistry · 2003 · 36 citations · Full text

, , +17

Synthesis and biological evaluation of aroylguanidines related to amiloride as inhibitors of the human platelet Na+/H+ exchanger

Didier Laeckmann · Bioorganic & Medicinal Chemistry · 2002 · 33 citations

, , +6