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Synthesis 2012(3): 377-379
DOI: 10.1055/s-0031-1289994
DOI: 10.1055/s-0031-1289994
SHORTPAPER
© Georg Thieme Verlag
Stuttgart ˙ New York
A Thiophosphoryl Chloride Assisted Transformation of Arylaldoximes to Thioamides
Further Information
Received
24 October 2011
Publication Date:
22 December 2011 (online)
Publication History
Publication Date:
22 December 2011 (online)
Abstract
Primary benzothioamides were accessed from benzaldoximes (benzaldehyde oximes) via benzonitriles in a sequential tandem approach utilizing thiophosphoryl chloride as a dehydrating and thionating agent.
Key words
primary thioamides - oximes - thiophosphoryl chloride - nitriles
-
1a
Metzner P. Synthesis 1992, 1185 -
1b
Haller HLJ, andBarthel WF. inventors; US 2,358,925. -
1c
Leresque CL. inventors; US 2,560,296. -
1d
Le Hir de Fallois LP,Lee HI, andTimmons PR. inventors; US 7964621. -
1e
Jagodzinski TS. Chem. Rev. 2003, 103: 197 -
1f
Lawesson SO.Perregaard J.Scheibye S.Meyer HJ.Thompson I. Bull. Soc. Chim. Belg. 1977, 86: 679 -
1g
Caddick, S. SyntheticPages [Online], 2001, DOI: 10.1039/SP66;
http://www.syntheticpages.org/pages/66. -
2a
Oare DA.Sanner MA.Heathcock CH. J. Org. Chem. 1990, 55: 132 -
2b
Heathcock CH.Davidson SK.Mills SG.Sanner MA. J. Org. Chem. 1992, 57: 2531 -
2c
Magnus P.Mendoza JS.Stamford A.Ladlow M.Willis P. J. Am. Chem. Soc. 1992, 114: 10232 -
2d
Kim G.Chu-Moyer MY.Danishefsky SJ.Schulte GK. J. Am. Chem. Soc. 1993, 115: 30 -
2e
Takahata H.Banba Y.Mozumi M.Yamazaki T. Heterocycles 1986, 24: 947 -
2f
Takahata H.Yamazaki T. Heterocycles 1988, 27: 1953 -
2g
Hurd RN.Delmater GT. Chem. Rev 1961, 61: 45 -
3a
Mahammed KA.Jayashankara VP.Premsai Rai N.Mohana Raju K.Arunachalam PN. Synlett 2009, 2338 ; and references therein -
3b
Kaboudin B.Elhamifar D. Synthesis 2006, 224 -
3c
Cho D.Ahn J.De Castro KA.Ahn H.Hakjune R. Tetrahedron 2010, 66: 5583 ; and references therein -
3d
Bergman J.Pettersson B.Hasimbegovic V.Svensson PH. J. Org. Chem. 2011, 76: 1546 -
3e
Kaboudin B.Malekzadeh L. Synthesis 2011, 2807 - 4
Wan J.-P.Liu Y. Synthesis 2010, 3943 -
5a
Sardarian AR.Shahsavari-Fard Z.Shahsavari HR.Ebrahimi Z. Tetrahedron Lett. 2007, 48: 2639 ; and references therein -
5b
Li Z.Lu Z.Zhu A.Feng X.Liu J.Tian G. Catal. Lett. 2008, 120: 105 -
5c
Kokare ND.Shinde DB. Monatsh. Chem. 2009, 140: 185 -
5d
Niknam K.Karami B.Kiasat AR. Bull. Korean Chem. Soc. 2005, 26: 975 -
5e
Iranpoor N.Firouzabadi H.Arezu J.Mana T. Lett. Org. Chem. 2006, 3: 267 -
5f
Noei J.Khosropour AR. Tetrahedron Lett. 2008, 49: 6969 -
6a
Yang C.Sun D. Asian J. Chem. 2011, 23: 2112 -
6b
Fee DC.Gard DR.Yang C. Phosphorus Compounds, In Kirk-Othmer Encyclopedia of Chemical Technology John Wiley & Sons; New York: 2005. -
6c
Pathak U.Pandey LK.Tank R. J. Org. Chem. 2008, 73: 2890 - 7
Vimal M.Pathak U.Pandey LK.Suryanarayana MVS. Synthesis 2011, 30 - 8
Kaboudin B.Elhamifar D. Synthesis 2006, 224 - 9
Lin P.-Y.Ku W.-S.Shiao M.-J. Synthesis 1992, 1219 - 10
Nagl M.Panuschka C.Barta A.Schmid W. Synthesis 2008, 4012 - 11
Bagley MC.Chapaneri K.Glover C.Merritt EA. Synlett 2004, 2615 - 12
Crane LJ.Anastassiadou M.Stigliani J.-L.Baziard-Mouysset G.Payard M. Tetrahedron 2004, 60: 5325 -
13a
Hajipour AR.Mallakpour SE.Imanzadeh G. J. Chem. Res., Synop. 1999, 228 -
13b
Hajipour AR.Rafiee F.Ruoho AE. J. Iran. Chem. Soc. 2011, 7: 114 -
13c
Li J.-T.Chen Y.-X.Li X.-L.Deng H.-J. Asian J. Chem. 2007, 19: 2236 -
13d
Yates J,Willcox TJ,Wood DA, andHaken PT. inventors; US 3,129,260.