One-pot synthesis of isocyanides from alcohols

Synthesis

Volumn , Issue 24, 2011, Pages 3997-4002

  Okada, Iku ^a   Kitano, Yoshikazu ^a  

^a TOKYO UNIVERSITY OF AGRICULTURE AND TECHNOLOGY   (Japan)

Author keywords

alcohols; isocyanides; Ritter reactions

Indexed keywords

BENZYLIC; ISOCYANIDES; METHANE SULFONIC ACID; ONE-POT REACTION; ONE-POT SYNTHESIS; RITTER REACTIONS; TRIETHYLAMINES; TRIMETHYLSILYL CYANIDE;

ALCOHOLS; CHLORINE COMPOUNDS; SYNTHESIS (CHEMICAL);

CYANIDES;

ALCOHOL DERIVATIVE; CYANAMIDE; FORMAMIDE; MESYLIC ACID; PYRIDINE; TRIETHYLAMINE;

ARTICLE; CHEMICAL REACTION; ONE POT SYNTHESIS; PROCESS OPTIMIZATION;

EID: 82955187345     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0031-1289592     Document Type: Article

References (39)

1. Passerini M, Gazz. Chim. Ital. 1921 51 126
2. Ugi I, Betz W, Fetzer U, Offerman K, Chem. Ber. 1961 94 2814
3. Isonitrile Chemistry Ugi I Academic Press New York 1971
4. Dömling A, Ugi I, Angew. Chem. Int. Ed. 2000 39 3168
5. Ugi I, Dömling A, In Combinatorial Chemistry: A Practical Approach Fenniri H Oxford University Press Oxford 2000 287
6. Dömling A, Curr. Opin. Chem. Biol. 2000 4 318
7. Ugi I, Werner B, Dömling A, In Targets in Heterocyclic Systems: Chemistry and Properties Attanasi O A. Filippone P Società Chimica Italiana Rome 2000
8. Li X, Danishefsky S J., J. Am. Chem. Soc. 2008 130 5446
9. Li X, Danishefsky S J., Nat. Protoc. 2008 3 1666
10. Li X, Yuan Y, Berkowitz W F., Todaro L J., Danishefsky S J., J. Am. Chem. Soc. 2008 130 13222
11. Li X, Yuan Y, Kan C, Danishefsky S J., J. Am. Chem. Soc. 2008 130 13225
12. Wu X, Li X, Danishefsky S J., Tetrahedron Lett. 2009 50 1523
13. Yuan Y, Zhu J, Li X, Wu X, Danishefsky S J., Tetrahedron Lett. 2009 50 2329
14. Rao Y, Li X, Danishefsky S J., J. Am. Chem. Soc. 2009 131 12924
15. Wu X, Stocdill J L., Wang P, Danishefsky S J., J. Am. Chem. Soc. 2010 132 4098
16. Wu X, Park P K., Danishefsky S J., J. Am. Chem. Soc. 2011 133 7700
17. Fusetani N, Nat. Prod. Rep. 2004 21 94
18. Garson M J., Simpson J S., Nat. Prod. Rep. 2004 21 164
19. Kitano Y, Ito T, Suzuki T, Nogata Y, Shinshima K, Yoshimura E, Chiba K, Tada M, Sakaguchi I, J. Chem. Soc., Perkin Trans. 1 2002 2251
20. Kitano Y, Yokoyama A, Nogata Y, Shinshima K, Yoshimura E, Chiba K, Tada M, Sakaguchi I, Biofouling 2003 19 (Suppl.1) 187
21. Nogata Y, Kitano Y, Yoshimura E, Shinshima K, Sakaguchi I, Biofouling 2004 20 87
22. Kitano Y, Nogata Y, Shinshima K, Yoshimura E, Chiba K, Tada M, Sakaguchi I, Biofouling 2004 20 93
23. Kitano Y, Akima C, Yoshimura E, Nogata Y, Biofouling 2011 27 201
24. Baldwin J E., ONeil I A., Synlett 1990 603
25. Launay D, Booth S, Clemens I, Merritt A, Bradley M, Tetrahedron Lett. 2002 43 7201
26. Porcheddu A, Giacomelli G, Salaris M, J. Org. Chem. 2005 70 2361
27. Kim S, Yi K Y., Tetrahedron Lett. 1986 27 1925
28. Creedon S M., Crowley H K., McCarthy D G., J. Chem. Soc., Perkin Trans. 1 1998 1015
29. Bose D S., Goud P R., Tetrahedron Lett. 1999 40 747
30. Kitano Y, Chiba K, Tada M, Tetrahedron Lett. 1998 39 1911
31. Kitano Y, Chiba K, Tada M, Synthesis 2001 437
32. Chen H G., Goel O P., Kesten S, Knobelsdolf J, Tetrahedron Lett. 1996 37 8129
33. Booth M R., Frankiss S G., J. Chem. Soc., Chem. Commun. 1968 1347
34. Reetz M T., Chatziiosifidis I, Künzer H, Müller-Starke H, Tetrahedron 1983 39 961
35. Zieger H E., Wo S, J. Org. Chem. 1994 59 3838
36. Sasaki T, Eguchi S, Katada T, J. Org. Chem. 1974 39 1239
37. Kobayashi G, Saito T, Kitano Y, Synthesis 2011 3225
38. Kitano Y, Manoda T, Miura T, Chiba K, Tada M, Synthesis 2006 405
39. Kitano Y, Nogata Y, Matsumura K, Yoshimura E, Chiba K, Tada M, Sakaguchi I, Tetrahedron 2005 61 9969