An efficient synthesis of cyanoarenes and cyanoheteroarenes via lithiation followed by electrophilic cyanation

Tetrahedron

Volumn 59, Issue 31, 2003, Pages 5831-5836

  Sato, Nobuhiro ^a   Yue, Qi ^a  

^a YOKOHAMA CITY UNIVERSITY   (Japan)

Author keywords

Cyano arenes; Electrophilic cyanation; Lithiation; Phenyl cyanate

Indexed keywords

2 (4',4' DIMETHYL 2' OXAZOLINYL)BENZONITRILE; 2 (4',4' DIMETHYL 2' OXAZOLINYL)THIOPHENE 3 CARBONITRILE; 2 (METHOXYMETHYL)OXYBENZONITRILE; 4 (N PIVALOYLAMINO)PYRIDINE 3 CARBONITRILE; BENZONITRILE; CYANIC ACID DERIVATIVE; HALOGEN; LITHIUM; N (TERT BUTOXYCARBONYL) 2 AMINOBENZONITRILE; N (TERT BUTOXYCARBONYL) 2 AMINOPYRIDINE 3 CARBONITRILE; N (TERT BUTOXYCARBONYL) 3 AMINOPYRIDINE 4 CARBONITRILE; N (TERT BUTOXYCARBONYL) 4 AMINOPYRIDINE 3 CARBONITRILE; N (TERT BUTOXYCARBONYL) 5 AMINOFURAN 2 CARBONITRILE; N (TERT BUTOXYCARBONYL) 5 AMINOTHIOPENE 2 CARBONITRILE; N,N DIETHYL 2 CYANOBENZENESULFAMIDE; N,N DIISOPROPYL 2 CYANOBENZAMIDE; N,N DIISOPROPYL 3 CYANOFURAN 2 CARBOXAMIDE; NITRILE; POLYCYCLIC AROMATIC HYDROCARBON; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; CYANATION; LITHIATION; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; QUANTUM YIELD; SYNTHESIS;

EID: 0038783758     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(03)00985-2     Document Type: Article

References (36)

1. For recent examples see: Undheim K., Benneche T. Katritzky A.R., Rees C.W., Scriven E.F.V. Pyrimidines and Their Benzo Derivatives. Comprehensive Heterocyclic Chemistry II. Vol. 6:1996;208-213 Pergamon, Oxford.
2. Adachi M., Sugasawa T. Synth. Commun. 20:1990;71-84.
3. (a) Schlosser M. Organoalkali Chemistry. Schlosser M. Organometallics in Synthesis. A Manual. 2002;251-265 Wiley, Baffins Lane,
4. (b) Clayden J. Baldwin J.E., Williams R.M. Selectivity for Synthesis. Tetrahedron Organic Chemistry Series. Vol. 23:2002;28-85 Pergamon, Amsterdam.
5. Preliminary publication: Sato N. Tetrahedron Lett. 43:2002;6403-6404.
6. Zweifel G., Snow J.T., Whitney C.C. J. Am. Chem. Soc. 90:1968;7139-7141.
7. Wheland R.C., Martin E.L. J. Org. Chem. 40:1975;3101-3109.
8. Van Leusen A.M., Jagt J.C. Tetrahedron Lett. 11:1970;967-970.
9. Klement I., Lennick K., Tucker C.E., Knochel P. Tetrahedron Lett. 34:1993;4623-4626.
10. Stadtmueller H., Greve B., Lennick K., Chair A., Knochel P. Synthesis. 1995;69-72.
11. Murray R.E., Zweifel G. Synthesis. 1980;150-151.
12. Davis W.A., Cava M.P. J. Org. Chem. 48:1983;2774-2775.
13. Foulger N.J., Wakefield B.J. Tetrahedron Lett. 13:1972;4169-4170.
14. Hughes T.V., Hammond S.D., Cava M.P. J. Org. Chem. 63:1998;401-402.
15. Hughes T.V., Cava M.P. J. Org. Chem. 64:1999;313-315.
16. Wu Y.-q., Limburg D.C., Wilkinson D.E., Hamilton G.S. Org. Lett. 2:2000;795-797.
17. Martin D., Bauer M. Organic Syntheses. Collect. Vol. No. 7:1990;Wiley, New York. pp 435-438.
18. Evans P.A., Nelson J.D., Stanley A.L. J. Org. Chem. 60:1995;2298-2301.
19. Grigat E., Pütter R. Chem. Ber. 97:1964;3012-3017.
20. Watanabe H., Schwarz R.A., Hauser C.R., Lewis J., Slocum D.W. Can. J. Chem. 47:1969;1543-1546.
21. Stanetty P., Koller H., Mihovilovic M. J. Org. Chem. 57:1992;6833-6837.
22. Viswanathan C.T., Wilkie C.A. J. Organomet. Chem. 54:1973;1-7.
23. Turner J.A. J. Org. Chem. 48:1983;3401-3408.
24. Carpenter A.J., Chadwick D.J. J. Chem. Soc., Perkin Trans. 1. 1985;173-181.
25. Fiakpui C.Y., Knaus E.E. Can. J. Chem. 65:1987;1158-1161.
26. The lithiation of 4a proceeded smoothly unlike the previous observation involving cleavage of the furan ring: Ref. Doadt E.G., Snieckus V. Tetrahedron Lett. 26:1985;1149-1152.
27. The same regioselectivity was observed in lithiation/electrophilic substitution of N-pivaloyl-3-aminopyridine or N-(t-butoxycarbonyl)-3-aminopyridine: Refs. 22,24.
28. Malmberg H., Nilsson M. Tetrahedron. 42:1986;3981-3986.
29. Savoia D., Concialini V., Roffia S., Tarsi L. J. Org. Chem. 56:1991;1822-1827.
30. Savage S.A., Smith A.P., Fraser C.L. J. Org. Chem. 63:1998;10048-10051.
31. Rahm F., Stranne R., Bremberg U., Nordström K., Cernerud M., Macedo E., Moberg C. J. Chem. Soc., Perkin Trans. 1. 2000;1983-1990.
32. Berillon L., Leprêtre A., Turck A., Plé N., Quéguiner G., Cahiez G., Knochel P. Synlett. 1998;1359-1360.
33. Abarbri M., Knochel P. Synlett. 1999;1577-1578.
34. Abarbri M., Thibonnet J., Bérillon L., Dehmel F., Rottländer M., Knochel P. J. Org. Chem. 65:2000;4618-4634.
35. Yang X., Rotter T., Piazza C., Knochel P. Org. Lett. 5:2003;1229-1231.
36. Juaristi E., Martines-Richa A., Garcia-Rivera A., Cruz-Sánchez J.S. J. Org. Chem. 48:1983;2603-2606.