A simple and efficient thiocyanation of indoles, anilines and keto compounds catalyzed by a polystyrene resin amberlyst-15

Letters in Organic Chemistry

Volumn 7, Issue 5, 2010, Pages 392-395

  Lenin, Racha ^a   Raju, Rallabandi M ^a  

^a OSMANIA UNIVERSITY   (India)

Author keywords

Amberlyst 15; Amines; Ammonium thiocyanate; Indoles; Ketones; Pyrrole

Indexed keywords

EID: 77955945517     PISSN: 15701786     EISSN: None     Source Type: Journal    
DOI: 10.2174/157017810791514878     Document Type: Article

References (18)

1. Guy, R.G. The Chemistry of Cyanates and their thioderivatives: Part 2, Chapt. 18, Patai, S: Ed: John Wiles & Sons: New York, 1977, p. 819.
2. (a) Wood, J. L. Organic Reactions: Wiles, New York, 1946, Vol. 3, 240.
3. (b) Kelly, T. R.; Kim, M. H.; Cetris, A. D. M. Structure Correction and Synthesis of the naturally occurring benzothiazinone BMY 40662. J. Org. Chem., 1993, 58, 5855.
4. Falck, J. R.; Gao, S.; Prasad, R. N.; Reddy, K. S. Electrophilic α - Thiocyanation of chiral and achiral N-acyl imides: a convenient route to 5-substituted and 5,5-disubsituted 2,4-thiazolidinediones. Bioorg. Med. Chem. Lett., 2008, 18, 1768.
5. 4NSCN system. Tetrahedron, 2006, 62, 5498.
6. (a) Yadav, J. S.; Reddy, B. V. S.; Reddy, U. V. S.; Krishna, A. D. Iodine /MeOH as a novel and versatile reagent system for the synthesis of α - ketothiocyanates. Tetrahedron Lett., 2007, 48, 5243.
7. (b) Koser, G. F.; Telu, S.; Laali, K. K. Oxidative-substitution reactions of polycyclic aromatic hydrocarbons with iodine (III) sulfonate reagents. Tetrahedron Lett., 2006, 47, 7011.
8. (a) Wu, G.; Liu, Q.; Sheu, Y.; Wu, W.; Wu, L. Regioselective thiocyanation of aromatic and heteroaromatic compounds using ammonium thiocyanate and oxone. Tetrahedron Lett., 2005, 46, 5831.
9. (b) Kumar, A.; Ahamd, P.; Maurya, R. A. Direct α - thiocyanation of carbonyl and β-dicarbonyl compounds using potassium peroxydisulfate- copper(II). Tetraedron Lett., 2007, 48, 1399.
10. (c) Pezzella, A.; Palma, A.; Iadonisi, A.; Napolitano, A.; d'Ischia, M. The first entry to 5,6-dihydroxy-3-mercaptoindole, 5-hydroxy-3-mercaptoindole and their 2-carbomethoxy derivatives by a mild thiocyanation/reduction methodology. Tetrahedron Lett., 2007, 48, 3883.
11. (a) Chakrabarty, M.; Sarkar, S. A clay-mediated eco-friendly thiocyanation of indoles and carbazoles. Tetrahedron Lett., 2003, 44, 8131.
12. (b) Nair, V.; George, T. G.; Nair, L. G.; Panicker, S. B. A direct synthesis of aryl thiocyanates using cerium(IV) ammonium nitrate. Tetrahedron Lett., 1999, 40, 1195.
13. (a) Renard, P. Y.; Schwebel, H.; Vayron, P.; Leclerc, E.; Dias, S.; Mioskowski, C. Optimized access to alkyl thiocyanates. Tetrahedron Lett., 2001, 42, 8479.
14. 2. Chem. Lett., 1998, 1091.
15. (c) Yadav, J. S.; Reddy, B. V. S.; Krishna, A. D.; Reddy, C. S.; Narsaiah, A. V. Ferric(III) Chloride-promoted electrophilic thiocyanation of aromatic and heteroaromatic compounds. Synthesis., 2005, 961.
16. (a) Yadav, J. S.; Reddy, B. V. S.; Sekar, K. C.; Sekar, D. G. Amberlyst-15 catalyzed novel synthesis of tetrahydropyranols. Synthesis, 2001, 885.
17. (b) Kalena, G. P.; Jain, A.; Benerji, A. Amberlyst 15 catalyzed prenylation of phenols: One -step synthesis of benzopyrans. Molecules, 1997, 100.
18. Lenin, R.; Madhusudhan Raju, R. Lanthanum trichloride: an efficient Lewis acid catalyst for chemo and regioselective enamination of β-dicarbonyl compounds. ARKIVOC, 2007, XIII, 204.