Substituted 3, 4-pyridynes: clean cycloadditions

SJ Connon, AF Hegarty

Index: Connon, Stephen J.; Hegarty, Anthony F. Journal of the Chemical Society, Perkin Transactions 1, 2000 , # 8 p. 1245 - 1249

Full Text: HTML

Citation Number: 23

Abstract

The stabilisation of 3, 4-pyridyne (1) by an alkoxy group adjacent to the ring nitrogen is reported. The regioselective lithiation of 2-ethoxy-(14), 2-methoxy-(18), 2-isopropoxy-(19) and 6-isopropoxy-(26)-3-chloropyridines with tert-butyllithium at low temperatures, followed by elimination of lithium chloride affords 2-and 6-alkoxy-3, 4-pyridynes. These species are trapped in situ with furan in a Diels–Alder reaction to give 5–8 in 66–89% yield, and do not ...

Related Articles:

Rapid room temperature Buchwald–Hartwig and Suzuki–Miyaura couplings of heteroaromatic compounds employing low catalyst loadings

[Navarro, Oscar; Marion, Nicolas; Mei, Jianguo; Nolan, Steven P. Chemistry - A European Journal, 2006 , vol. 12, # 19 p. 5142 - 5148]

Synthesis of aminopyridines from 2-fluoropyridine and lithium amides

[Pasumansky, Lubov; Hernandez, Armando R.; Gamsey, Soya; Goralski, Christian T.; Singaram, Bakthan Tetrahedron Letters, 2004 , vol. 45, # 34 p. 6417 - 6420]

Photocatalyzed [2+ 2+ 2]-cycloaddition of nitriles with acetylene: an effective method for the synthesis of 2-pyridines under mild conditions

[Heller, Barbara; Sundermann, Bernd; Buschmann, Helmut; Drexler, Hans-Joachim; You, Jingsong; Holzgrabe, Ulrike; Heller, Eberhard; Oehme, Guenther Journal of Organic Chemistry, 2002 , vol. 67, # 13 p. 4414 - 4422]

A mild, catalyst-free synthesis of 2-aminopyridines

[Poola, Bhaskar; Choung, Wonken; Nantz, Michael H. Tetrahedron, 2008 , vol. 64, # 48 p. 10798 - 10801]

Microwave??promoted piperidination of halopyridines: a comparison between Ullmann, Buchwald–Hartwig and uncatalysed SNAr reactions

[Yaunner, Ricardo S.; Barros, Jose C.; Da Silva, Joaquim F. M. Applied Organometallic Chemistry, 2012 , vol. 26, # 6 p. 273 - 276]

More Articles...