Abstract
Indoles, oxindoles and aromatic amino compounds undergo smooth thiocyanation with ammonium thiocyanate in the presence of anhydrous FeCl3 in dichloromethane under mild conditions to afford the corresponding 3-indolyl and 4-aryl thiocyanates, respectively, in high yields with excellent selectivity. The use of ferric chloride makes it quite simple, more convenient and practical. This new method offers several advantages such as high conversions, cleaner reaction profiles, short reaction times, and the use of inexpensive and readily available catalyst.
Key words
thiocyanation - electrophilic substitution - aromatic systems - aryl thiocyanates
References 1 IICT Communication No: 041214.
2a
Wood JL.
Org. React.
1946,
3:
240
2b
Kelly TR.
Kim MH.
Curtis ADM.
J. Org. Chem.
1993,
58:
5855
3
Guy RG. In
The Chemistry of Cyanates and Their Thio Derivatives
Part 2:
Patai S.
Wiley;
New York:
1977.
Chap. 18.
p.819
4a
Toste FD.
Laronde F.
Still WJ.
Tetrahedron Lett.
1995,
36:
2949
4b
Grant MS.
Snyder HR.
J. Am. Chem. Soc.
1960,
82:
2742
5a
Kita Y.
Takeda T.
Mihara S.
Whelan BA.
Thoma H.
J. Org. Chem.
1995,
60:
7144
5b
Yadav JS.
Reddy BVS.
Shubashree S.
Sadashiv K.
Tetrahedron Lett.
2004,
45:
2951
6a
Toste FD.
De Stefano V.
Still WJ.
Synth. Commun.
1995,
25:
1277
6b
Nair V.
George TG.
Nair LG.
Panicker SB.
Tetrahedron Lett.
1999,
40:
1195
7
Chakrabarty M.
Sarkar S.
Tetrahedron Lett.
2003,
44:
8131
8a
Christoffers J.
J. Chem. Soc., Perkin Trans. 1
1997,
3141
8b
Christoffers J.
Oertling H.
Tetrahedron
2000,
56:
1339
8c
Lu J.
Ma H.
Synlett
2000,
63
8d
Masson C.
Soto J.
Bessodes M.
Synlett
2000,
1281
8e
Chibiryaev AM.
Kimpe ND.
Tkachev AV.
Tetrahedron Lett.
2000,
41:
8011