Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Synthesis 2009(5): 713-714
DOI: 10.1055/s-0028-1083348
DOI: 10.1055/s-0028-1083348
SHORTPAPER
© Georg Thieme Verlag
Stuttgart ˙ New York
Convenient Multigram Synthesis of 4-Chloropyridine-2,6-dicarbonyl Dichloride
Further Information
Received
12 September 2008
Publication Date:
02 February 2009 (online)
Publication History
Publication Date:
02 February 2009 (online)
Abstract
A method amenable to the multigram-scale preparation of 4-chloropyridine-2,6-dicarbonyl dichloride is described. The key transformation is the deoxygenative chlorination of the pyridine N-oxide with oxalyl choride.
Key words
4-chloropyridine-2,6-dicarbonyl dichloride - supramolecular chemistry - deoxygenative chlorination - carboxylic acid chlorides - nitrogen heterocycles
-
1a
Tse MK.Bhor S.Klawonn M.Anilkumar G.Jiao H.Döbler C.Spannenberg A.Mägerlein W.Hugl H.Beller M. Chem. Eur. J. 2006, 12: 1855 -
1b
Cornejo A.Fraile JM.Garcia JI.Gil MJ.Luis SV.Martinez-Merino V.Mayoral JA. J. Org. Chem. 2005, 70: 5536 -
1c
Barsu C.Fortrie R.Nowika K.Baldeck PL.Vial J.-C.Barsella A.Fort A.Hissler M.Bretonniere Y.Maury O.Andraud C. Chem. Commun. 2006, 4744 -
2a
Hisamatsu Y.Hasada K.Amano F.Tsubota Y.Wasada-Tsutsui Y.Shirai N.Ikeda S.Odashima K. Chem. Eur. J. 2006, 12: 7733 -
2b
Chae MK.Cha G.-Y.Jeong K.-S. Tetrahedron Lett. 2006, 47: 8217 -
2c
Haino T.Fujii T.Fukazawa Y. J. Org. Chem. 2006, 71: 2572 -
2d
Chang S.-Y.Kim HS.Chang K.-J.Jeong K.-S. Org. Lett. 2004, 6: 181 -
3a
Hong F.Hollenback D.Singer JW.Klein P. Bioorg. Med. Chem. Lett. 2005, 15: 4703 -
3b
Bhattacharya S.Snehalatha K.Kumar VP. J. Org. Chem. 2003, 68: 2741 -
3c
Kurosaki H.Sharma RK.Aoki S.Inoue T.Okamoto Y.Sugiura Y.Doi M.Ishida T.Otsuka M.Goto M. J. Chem. Soc., Dalton Trans. 2001, 441 -
4a
Gabriel CJ.Parquette JR. J. Am. Chem. Soc. 2006, 128: 13708 -
4b
Huang B.Prantil MA.Gustafson TL.Parquette JR. J. Am. Chem. Soc. 2003, 125: 14518 -
4c
Hofacker AL.Parquette JR. Angew. Chem. Int. Ed. 2005, 44: 1053 -
5a
Riegel R.Zwilgmeyer D. Org. Synth. Coll. Vol. II 1950, 126 -
5b
Fibel LR.Spoerri PE. J. Am. Chem. Soc. 1948, 70: 3908 -
5c
Toomey RF.Riegel ER. J. Org. Chem. 1952, 17: 1492 -
5d
Harirchain B, andGormley JL. inventors; US Patent 5300657. ; Chem. Abstr. 1994, 121, 9159 -
5e
Horvath G.Rusa C.Kontos Z.Gerencser J.Huszthy P. Synth. Commun. 1999, 29: 3719 -
6a
Evans RF.Brown HC. J. Org. Chem. 1962, 27: 1329 -
6b
Hansen JF.Kim YI.Merrigan KA. J. Org. Chem. 1979, 44: 4438 -
6c
Bremner DH.Dunn AD.Wilson KA. Synthesis 1992, 6: 528 -
6d
Alcazar J.Alonso JM.Bartolome JM.Iturino L.Matesanz E. Tetrahedron Lett. 2003, 44: 8983 -
6e
Thibault C.L’Heureux A.Bhide RS.Ruel R. Org. Lett. 2003, 5: 5023 -
7a
Syper L.Kloc K.Mlochowski J.Szulc Z. Synthesis 1979, 521 -
7b
Thummel RP.Chirayil S.Hery C.Lim J.-L.Wang T.-L. J. Org. Chem. 1993, 58: 1666 - 8
Recker J.Tomcik DJ.Parquette JR. J. Am. Chem. Soc. 2000, 122: 10298 - 9
Markees DG. J. Org. Chem. 1958, 23: 1030