A Facile Nucleophilic Displacement of Baylis-Hillman Acetates with Ammonium­ Thiocyanate

Pabbaraja Srihari; Ashutosh Pratap Singh; Ruchi Jain; Jhillu Singh Yadav

doi:10.1055/s-2006-942479

PAPER

A Facile Nucleophilic Displacement of Baylis-Hillman Acetates with Ammonium Thiocyanate

Pabbaraja Srihari*, Ashutosh Pratap Singh, Ruchi Jain, Jhillu Singh Yadav
Organic Division I, Indian Institute of Chemical Technology, Hyderabad 500007, India
Fax: +91(40)27160512; e-Mail: srihari@iict.res.in;

Abstract

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Abstract

Baylis-Hillman acetates undergo smooth nucleophilic displacement with ammonium thiocyanate under mild basic conditions in quantitative yields.

Key words

Baylis-Hillman acetate - ammonium thiocyanate - nucleophiles - thiazoles - thiocyanates

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References

<A NAME="RZ05906SS-1">1</A> Schulze B. Muhlstadt M. Schubert I. Z. Chem. 1979, 19: 41

<A NAME="RZ05906SS-2A">2a</A> Toste FD. Laronde F. Still WJ. Tetrahedron Lett. 1995, 36: 2949

<A NAME="RZ05906SS-2B">2b</A> Grant MS. Snyder HR. J. Am. Chem. Soc. 1960, 82: 2742

<A NAME="RZ05906SS-3A">3a</A> Wood JL. Org. React. 1946, 3: 240

<A NAME="RZ05906SS-3B">3b</A> Guy RG. In The Chemistry of Cyanates and Their Thio Derivatives, Part 2 Patai S. Wiley; New York: 1977. Chap. 18. p.819

<A NAME="RZ05906SS-4A">4a</A> Baylis AB, and Hillman MED. inventors; DE 2,155,113. ; Chem. Abstr., 1972, 77, 34174q

<A NAME="RZ05906SS-4B">4b</A> Ghosh AK. Bilcer G. Schiltz G. Synthesis 2001, 2203

<A NAME="RZ05906SS-4C">4c</A> List B. Castello C. Synlett 2001, 1687

<A NAME="RZ05906SS-5">5</A> Irgolic KJ. In Houben-Weyl 4th ed., Vol. E 12b: Klamann D. Thieme; Stuttgart: 1990. p.150

<A NAME="RZ05906SS-6A">6a</A> Lee KY. Kim JM. Kim JN. Tetrahedron Lett. 2003, 44: 6737

<A NAME="RZ05906SS-6B">6b</A> Lee KY. Kim JM. Kim JN. Tetrahedron 2003, 59: 385

<A NAME="RZ05906SS-6C">6c</A> Kim JN. Kim JM. Lee KY. Synlett 2003, 821

<A NAME="RZ05906SS-6D">6d</A> Kim JN. Kim HS. Gong JH. Chung YM. Tetrahedron Lett. 2001, 42: 8341

<A NAME="RZ05906SS-6E">6e</A> Hoffmann HMR. Rabe J. Helv. Chim. Acta 1984, 67: 413

<A NAME="RZ05906SS-6F">6f</A> Hoffman HMR. Rabe J. Angew. Chem., Int. Ed. Engl. 1985, 24: 94

<A NAME="RZ05906SS-7A">7a</A> Basavaiah D. Dharma Rao P. Suguna HR. Tetrahedron 1996, 52: 8001

<A NAME="RZ05906SS-7B">7b</A> Yadav JS. Gupta MK. Pandey SK. Reddy BVS. Sarma AVS. Tetrahedron Lett. 2005, 46: 2761

<A NAME="RZ05906SS-7C">7c</A> Fuocaud A. EI Guemmount F. Bull. Soc. Chim. Fr. 1989, 403

<A NAME="RZ05906SS-8A">8a</A> Basavaiah D. Suguna HR. Muthukumaran K. Kumaragurubaran N. Synthesis 2000, 217

<A NAME="RZ05906SS-8B">8b</A> For phenols, see: Roy O. Riahi A. Henin F. Muzart J. Tetrahedron 2000, 56: 8133

<A NAME="RZ05906SS-9A">9a</A> Basavaiah D. Satyanarayana T. Tetrahedron Lett. 2002, 43: 4301

<A NAME="RZ05906SS-9B">9b</A> Kundu MK. Bhat SV. Synth. Commun. 1999, 29: 93

<A NAME="RZ05906SS-9C">9c</A> Hbaieb S. Latiri Z. Amri H. Synth. Commun. 1999, 29: 981

<A NAME="RZ05906SS-10A">10a</A> Basavaiah D. Bhavani AKD. Pandiaraju S. Sarma PKS. Synlett 1995, 243

<A NAME="RZ05906SS-10B">10b</A> Basavaiah D. Jaganmohan Rao A. Satyanarayana T. Chem. Rev. 2003, 103: 811 ; and references cited therein

<A NAME="RZ05906SS-11A">11a</A> Basavaiah D. Sarma PKS. J. Chem. Soc., Chem. Commun. 1992, 955

<A NAME="RZ05906SS-11B">11b</A> Rabe J. Hoffmann HMR. Angew. Chem., Int. Ed. Engl. 1983, 22: 796

<A NAME="RZ05906SS-11C">11c</A> Hoffmann HMR. Rabe J. J. Org. Chem. 1985, 50: 3849

<A NAME="RZ05906SS-11D">11d</A> Im YJ. Kim JM. Mun JH. Kim JN. Bull. Korean Chem. Soc. 2001, 22: 349

<A NAME="RZ05906SS-12A">12a</A> Kim JN. Chung YM. Im YJ. Tetrahedron Lett. 2002, 43: 6209

<A NAME="RZ05906SS-12B">12b</A> Chung YM. Lee HJ. Hwang SS. Kim JN. Bull. Korean Chem. Soc. 2001, 22: 799

<A NAME="RZ05906SS-13">13</A> Kamimura A. Morita R. Matsuura K. Omata Y. Shirai M. Tetrahedron Lett. 2002, 43: 6189

<A NAME="RZ05906SS-14A">14a</A> Yadav JS. Reddy BVS. Shubashree S. Sadashiv K. Tetrahedron Lett. 2004, 45: 2951

<A NAME="RZ05906SS-14B">14b</A> Yadav JS. Reddy BVS. Gupta MK. Synthesis 2004, 1983

For other contribution on aromatic and alkyl thiocyanation, see:

<A NAME="RZ05906SS-15A">15a</A> Niknam K. Phosphorus, Sulfur Silicon Relat. Elem. 2004, 179: 499

<A NAME="RZ05906SS-15B">15b</A> Karade NN. Tiwari GB. Shirodkar SG. Dhoot BM. Synth. Commun. 2005, 35: 1197

A Facile Nucleophilic Displacement of Baylis-Hillman Acetates with Ammonium­ Thiocyanate

A Facile Nucleophilic Displacement of Baylis-Hillman Acetates with Ammonium Thiocyanate