An Efficient Access to Selenazoline-4-Carboxylate Derivatives Incorporating Cyclopropyl Groups

Synlett

Volumn , Issue 2, 2004, Pages 329-331

  Huang, Xian ^a,b   Chen, Wan Li ^a   Zhou, Hong Wei ^a  

^a ZHEJIANG UNIVERSITY   (China)

^b SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

Michael addition; Selenium heterocycles; Selenoamide

Indexed keywords

CARBOXYLIC ACID DERIVATIVE; CYCLOPROPANE DERIVATIVE; SELENAZOLE DERIVATIVE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CYCLIZATION; DRUG STRUCTURE; DRUG SYNTHESIS; INFRARED SPECTROMETRY; MASS SPECTROMETRY; MICHAEL ADDITION; MOLECULAR DYNAMICS; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 1342302417     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2003-44969     Document Type: Article

References (46)

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31. For recent examples of selenoamides, see: (a) Pan, B. C.; Chen, Z. H.; Piras, G.; Dutschman, G. E.; Rowe, E. C.; Cheng, Y. C.; Ch, S. H. J. Heterocycl. Chem. 1994, 177. (b) Koketsu, M.; Senda, T.; Yoshimura, K.; Ishihara, H. J. Chem. Soc., Perkin Trans. 1 1999, 453. (c) Attanasi, O. A.; Filippone, P.; Perrulli, F. R.; Santeusanio, S. Eur. J. Org. Chem. 2002, 2323. (d) Koketsu, M. ; Takenaka, Y.; Hiramatsu, S.; Ishihara, H. Heterocycles 2001, 55, 1181. (e) Koketsu, M.; Hiramatsu, S.; Ishihara, H. Chem. Lett. 1999, 485. (f) Zhang, P. F.; Chen, Z. C. Synthesis 2000, 1219. (g) Koketsu, M.; Kanoh, M.; Itoh, E.; Ishihara, H. J. Org. Chem. 2001, 66, 4099. (h) Koketsu, M.; Takenaka, Y.; Ishihara, H. Synthesis 2001, 38, 503. (i) Zhang, P. F.; Chen, Z. C. J. Heterocycl. Chem. 2001, 38, 503. (j) Ishihara, H.; Koketsu, M.; Fukuta, Y.; Nada, F. J. Am. Chem. Soc. 2001, 123, 8408. (k) Bhattacharyya, P.; Woollins, J. D. Tetrahedron Lett. 2001, 42, 5949. (l) Koketsu, M.; Okayama, Y.; Aoki, H.; Ishihara, H. Heteroat. Chem. 2002, 13, 195. (m) Zhao, H.-R.; Zhao, X.-J.; Huang, X. Synth. Commun. 2002, 32, 3383.
32. For recent examples of selenoamides, see: (a) Pan, B. C.; Chen, Z. H.; Piras, G.; Dutschman, G. E.; Rowe, E. C.; Cheng, Y. C.; Ch, S. H. J. Heterocycl. Chem. 1994, 177. (b) Koketsu, M.; Senda, T.; Yoshimura, K.; Ishihara, H. J. Chem. Soc., Perkin Trans. 1 1999, 453. (c) Attanasi, O. A.; Filippone, P.; Perrulli, F. R.; Santeusanio, S. Eur. J. Org. Chem. 2002, 2323. (d) Koketsu, M. ; Takenaka, Y.; Hiramatsu, S.; Ishihara, H. Heterocycles 2001, 55, 1181. (e) Koketsu, M.; Hiramatsu, S.; Ishihara, H. Chem. Lett. 1999, 485. (f) Zhang, P. F.; Chen, Z. C. Synthesis 2000, 1219. (g) Koketsu, M.; Kanoh, M.; Itoh, E.; Ishihara, H. J. Org. Chem. 2001, 66, 4099. (h) Koketsu, M.; Takenaka, Y.; Ishihara, H. Synthesis 2001, 38, 503. (i) Zhang, P. F.; Chen, Z. C. J. Heterocycl. Chem. 2001, 38, 503. (j) Ishihara, H.; Koketsu, M.; Fukuta, Y.; Nada, F. J. Am. Chem. Soc. 2001, 123, 8408. (k) Bhattacharyya, P.; Woollins, J. D. Tetrahedron Lett. 2001, 42, 5949. (l) Koketsu, M.; Okayama, Y.; Aoki, H.; Ishihara, H. Heteroat. Chem. 2002, 13, 195. (m) Zhao, H.-R.; Zhao, X.-J.; Huang, X. Synth. Commun. 2002, 32, 3383.
33. For recent examples of selenoamides, see: (a) Pan, B. C.; Chen, Z. H.; Piras, G.; Dutschman, G. E.; Rowe, E. C.; Cheng, Y. C.; Ch, S. H. J. Heterocycl. Chem. 1994, 177. (b) Koketsu, M.; Senda, T.; Yoshimura, K.; Ishihara, H. J. Chem. Soc., Perkin Trans. 1 1999, 453. (c) Attanasi, O. A.; Filippone, P.; Perrulli, F. R.; Santeusanio, S. Eur. J. Org. Chem. 2002, 2323. (d) Koketsu, M. ; Takenaka, Y.; Hiramatsu, S.; Ishihara, H. Heterocycles 2001, 55, 1181. (e) Koketsu, M.; Hiramatsu, S.; Ishihara, H. Chem. Lett. 1999, 485. (f) Zhang, P. F.; Chen, Z. C. Synthesis 2000, 1219. (g) Koketsu, M.; Kanoh, M.; Itoh, E.; Ishihara, H. J. Org. Chem. 2001, 66, 4099. (h) Koketsu, M.; Takenaka, Y.; Ishihara, H. Synthesis 2001, 38, 503. (i) Zhang, P. F.; Chen, Z. C. J. Heterocycl. Chem. 2001, 38, 503. (j) Ishihara, H.; Koketsu, M.; Fukuta, Y.; Nada, F. J. Am. Chem. Soc. 2001, 123, 8408. (k) Bhattacharyya, P.; Woollins, J. D. Tetrahedron Lett. 2001, 42, 5949. (l) Koketsu, M.; Okayama, Y.; Aoki, H.; Ishihara, H. Heteroat. Chem. 2002, 13, 195. (m) Zhao, H.-R.; Zhao, X.-J.; Huang, X. Synth. Commun. 2002, 32, 3383.
34. For recent examples of selenoamides, see: (a) Pan, B. C.; Chen, Z. H.; Piras, G.; Dutschman, G. E.; Rowe, E. C.; Cheng, Y. C.; Ch, S. H. J. Heterocycl. Chem. 1994, 177. (b) Koketsu, M.; Senda, T.; Yoshimura, K.; Ishihara, H. J. Chem. Soc., Perkin Trans. 1 1999, 453. (c) Attanasi, O. A.; Filippone, P.; Perrulli, F. R.; Santeusanio, S. Eur. J. Org. Chem. 2002, 2323. (d) Koketsu, M. ; Takenaka, Y.; Hiramatsu, S.; Ishihara, H. Heterocycles 2001, 55, 1181. (e) Koketsu, M.; Hiramatsu, S.; Ishihara, H. Chem. Lett. 1999, 485. (f) Zhang, P. F.; Chen, Z. C. Synthesis 2000, 1219. (g) Koketsu, M.; Kanoh, M.; Itoh, E.; Ishihara, H. J. Org. Chem. 2001, 66, 4099. (h) Koketsu, M.; Takenaka, Y.; Ishihara, H. Synthesis 2001, 38, 503. (i) Zhang, P. F.; Chen, Z. C. J. Heterocycl. Chem. 2001, 38, 503. (j) Ishihara, H.; Koketsu, M.; Fukuta, Y.; Nada, F. J. Am. Chem. Soc. 2001, 123, 8408. (k) Bhattacharyya, P.; Woollins, J. D. Tetrahedron Lett. 2001, 42, 5949. (l) Koketsu, M.; Okayama, Y.; Aoki, H.; Ishihara, H. Heteroat. Chem. 2002, 13, 195. (m) Zhao, H.-R.; Zhao, X.-J.; Huang, X. Synth. Commun. 2002, 32, 3383.
35. For recent examples of selenoamides, see: (a) Pan, B. C.; Chen, Z. H.; Piras, G.; Dutschman, G. E.; Rowe, E. C.; Cheng, Y. C.; Ch, S. H. J. Heterocycl. Chem. 1994, 177. (b) Koketsu, M.; Senda, T.; Yoshimura, K.; Ishihara, H. J. Chem. Soc., Perkin Trans. 1 1999, 453. (c) Attanasi, O. A.; Filippone, P.; Perrulli, F. R.; Santeusanio, S. Eur. J. Org. Chem. 2002, 2323. (d) Koketsu, M. ; Takenaka, Y.; Hiramatsu, S.; Ishihara, H. Heterocycles 2001, 55, 1181. (e) Koketsu, M.; Hiramatsu, S.; Ishihara, H. Chem. Lett. 1999, 485. (f) Zhang, P. F.; Chen, Z. C. Synthesis 2000, 1219. (g) Koketsu, M.; Kanoh, M.; Itoh, E.; Ishihara, H. J. Org. Chem. 2001, 66, 4099. (h) Koketsu, M.; Takenaka, Y.; Ishihara, H. Synthesis 2001, 38, 503. (i) Zhang, P. F.; Chen, Z. C. J. Heterocycl. Chem. 2001, 38, 503. (j) Ishihara, H.; Koketsu, M.; Fukuta, Y.; Nada, F. J. Am. Chem. Soc. 2001, 123, 8408. (k) Bhattacharyya, P.; Woollins, J. D. Tetrahedron Lett. 2001, 42, 5949. (l) Koketsu, M.; Okayama, Y.; Aoki, H.; Ishihara, H. Heteroat. Chem. 2002, 13, 195. (m) Zhao, H.-R.; Zhao, X.-J.; Huang, X. Synth. Commun. 2002, 32, 3383.
36. For recent examples of selenoamides, see: (a) Pan, B. C.; Chen, Z. H.; Piras, G.; Dutschman, G. E.; Rowe, E. C.; Cheng, Y. C.; Ch, S. H. J. Heterocycl. Chem. 1994, 177. (b) Koketsu, M.; Senda, T.; Yoshimura, K.; Ishihara, H. J. Chem. Soc., Perkin Trans. 1 1999, 453. (c) Attanasi, O. A.; Filippone, P.; Perrulli, F. R.; Santeusanio, S. Eur. J. Org. Chem. 2002, 2323. (d) Koketsu, M. ; Takenaka, Y.; Hiramatsu, S.; Ishihara, H. Heterocycles 2001, 55, 1181. (e) Koketsu, M.; Hiramatsu, S.; Ishihara, H. Chem. Lett. 1999, 485. (f) Zhang, P. F.; Chen, Z. C. Synthesis 2000, 1219. (g) Koketsu, M.; Kanoh, M.; Itoh, E.; Ishihara, H. J. Org. Chem. 2001, 66, 4099. (h) Koketsu, M.; Takenaka, Y.; Ishihara, H. Synthesis 2001, 38, 503. (i) Zhang, P. F.; Chen, Z. C. J. Heterocycl. Chem. 2001, 38, 503. (j) Ishihara, H.; Koketsu, M.; Fukuta, Y.; Nada, F. J. Am. Chem. Soc. 2001, 123, 8408. (k) Bhattacharyya, P.; Woollins, J. D. Tetrahedron Lett. 2001, 42, 5949. (l) Koketsu, M.; Okayama, Y.; Aoki, H.; Ishihara, H. Heteroat. Chem. 2002, 13, 195. (m) Zhao, H.-R.; Zhao, X.-J.; Huang, X. Synth. Commun. 2002, 32, 3383.
37. For recent examples of selenoamides, see: (a) Pan, B. C.; Chen, Z. H.; Piras, G.; Dutschman, G. E.; Rowe, E. C.; Cheng, Y. C.; Ch, S. H. J. Heterocycl. Chem. 1994, 177. (b) Koketsu, M.; Senda, T.; Yoshimura, K.; Ishihara, H. J. Chem. Soc., Perkin Trans. 1 1999, 453. (c) Attanasi, O. A.; Filippone, P.; Perrulli, F. R.; Santeusanio, S. Eur. J. Org. Chem. 2002, 2323. (d) Koketsu, M. ; Takenaka, Y.; Hiramatsu, S.; Ishihara, H. Heterocycles 2001, 55, 1181. (e) Koketsu, M.; Hiramatsu, S.; Ishihara, H. Chem. Lett. 1999, 485. (f) Zhang, P. F.; Chen, Z. C. Synthesis 2000, 1219. (g) Koketsu, M.; Kanoh, M.; Itoh, E.; Ishihara, H. J. Org. Chem. 2001, 66, 4099. (h) Koketsu, M.; Takenaka, Y.; Ishihara, H. Synthesis 2001, 38, 503. (i) Zhang, P. F.; Chen, Z. C. J. Heterocycl. Chem. 2001, 38, 503. (j) Ishihara, H.; Koketsu, M.; Fukuta, Y.; Nada, F. J. Am. Chem. Soc. 2001, 123, 8408. (k) Bhattacharyya, P.; Woollins, J. D. Tetrahedron Lett. 2001, 42, 5949. (l) Koketsu, M.; Okayama, Y.; Aoki, H.; Ishihara, H. Heteroat. Chem. 2002, 13, 195. (m) Zhao, H.-R.; Zhao, X.-J.; Huang, X. Synth. Commun. 2002, 32, 3383.
38. For recent examples of selenoamides, see: (a) Pan, B. C.; Chen, Z. H.; Piras, G.; Dutschman, G. E.; Rowe, E. C.; Cheng, Y. C.; Ch, S. H. J. Heterocycl. Chem. 1994, 177. (b) Koketsu, M.; Senda, T.; Yoshimura, K.; Ishihara, H. J. Chem. Soc., Perkin Trans. 1 1999, 453. (c) Attanasi, O. A.; Filippone, P.; Perrulli, F. R.; Santeusanio, S. Eur. J. Org. Chem. 2002, 2323. (d) Koketsu, M. ; Takenaka, Y.; Hiramatsu, S.; Ishihara, H. Heterocycles 2001, 55, 1181. (e) Koketsu, M.; Hiramatsu, S.; Ishihara, H. Chem. Lett. 1999, 485. (f) Zhang, P. F.; Chen, Z. C. Synthesis 2000, 1219. (g) Koketsu, M.; Kanoh, M.; Itoh, E.; Ishihara, H. J. Org. Chem. 2001, 66, 4099. (h) Koketsu, M.; Takenaka, Y.; Ishihara, H. Synthesis 2001, 38, 503. (i) Zhang, P. F.; Chen, Z. C. J. Heterocycl. Chem. 2001, 38, 503. (j) Ishihara, H.; Koketsu, M.; Fukuta, Y.; Nada, F. J. Am. Chem. Soc. 2001, 123, 8408. (k) Bhattacharyya, P.; Woollins, J. D. Tetrahedron Lett. 2001, 42, 5949. (l) Koketsu, M.; Okayama, Y.; Aoki, H.; Ishihara, H. Heteroat. Chem. 2002, 13, 195. (m) Zhao, H.-R.; Zhao, X.-J.; Huang, X. Synth. Commun. 2002, 32, 3383.
39. For recent examples of selenoamides, see: (a) Pan, B. C.; Chen, Z. H.; Piras, G.; Dutschman, G. E.; Rowe, E. C.; Cheng, Y. C.; Ch, S. H. J. Heterocycl. Chem. 1994, 177. (b) Koketsu, M.; Senda, T.; Yoshimura, K.; Ishihara, H. J. Chem. Soc., Perkin Trans. 1 1999, 453. (c) Attanasi, O. A.; Filippone, P.; Perrulli, F. R.; Santeusanio, S. Eur. J. Org. Chem. 2002, 2323. (d) Koketsu, M. ; Takenaka, Y.; Hiramatsu, S.; Ishihara, H. Heterocycles 2001, 55, 1181. (e) Koketsu, M.; Hiramatsu, S.; Ishihara, H. Chem. Lett. 1999, 485. (f) Zhang, P. F.; Chen, Z. C. Synthesis 2000, 1219. (g) Koketsu, M.; Kanoh, M.; Itoh, E.; Ishihara, H. J. Org. Chem. 2001, 66, 4099. (h) Koketsu, M.; Takenaka, Y.; Ishihara, H. Synthesis 2001, 38, 503. (i) Zhang, P. F.; Chen, Z. C. J. Heterocycl. Chem. 2001, 38, 503. (j) Ishihara, H.; Koketsu, M.; Fukuta, Y.; Nada, F. J. Am. Chem. Soc. 2001, 123, 8408. (k) Bhattacharyya, P.; Woollins, J. D. Tetrahedron Lett. 2001, 42, 5949. (l) Koketsu, M.; Okayama, Y.; Aoki, H.; Ishihara, H. Heteroat. Chem. 2002, 13, 195. (m) Zhao, H.-R.; Zhao, X.-J.; Huang, X. Synth. Commun. 2002, 32, 3383.
40. For recent examples of selenoamides, see: (a) Pan, B. C.; Chen, Z. H.; Piras, G.; Dutschman, G. E.; Rowe, E. C.; Cheng, Y. C.; Ch, S. H. J. Heterocycl. Chem. 1994, 177. (b) Koketsu, M.; Senda, T.; Yoshimura, K.; Ishihara, H. J. Chem. Soc., Perkin Trans. 1 1999, 453. (c) Attanasi, O. A.; Filippone, P.; Perrulli, F. R.; Santeusanio, S. Eur. J. Org. Chem. 2002, 2323. (d) Koketsu, M. ; Takenaka, Y.; Hiramatsu, S.; Ishihara, H. Heterocycles 2001, 55, 1181. (e) Koketsu, M.; Hiramatsu, S.; Ishihara, H. Chem. Lett. 1999, 485. (f) Zhang, P. F.; Chen, Z. C. Synthesis 2000, 1219. (g) Koketsu, M.; Kanoh, M.; Itoh, E.; Ishihara, H. J. Org. Chem. 2001, 66, 4099. (h) Koketsu, M.; Takenaka, Y.; Ishihara, H. Synthesis 2001, 38, 503. (i) Zhang, P. F.; Chen, Z. C. J. Heterocycl. Chem. 2001, 38, 503. (j) Ishihara, H.; Koketsu, M.; Fukuta, Y.; Nada, F. J. Am. Chem. Soc. 2001, 123, 8408. (k) Bhattacharyya, P.; Woollins, J. D. Tetrahedron Lett. 2001, 42, 5949. (l) Koketsu, M.; Okayama, Y.; Aoki, H.; Ishihara, H. Heteroat. Chem. 2002, 13, 195. (m) Zhao, H.-R.; Zhao, X.-J.; Huang, X. Synth. Commun. 2002, 32, 3383.
41. abstract
42. (a) Huang, X.; Zhou, H. W. Org. Lett. 2002, 4, 4419.
43. (b) Zhou, H. W.; Huang, X.; Chen, W. L. Synlett 2003, 2080.
44. 2 (450 mg, 2 mmol) in MeCN (10 mL) was stirred under reflux and was monitored by TLC.
45. (a) Lai, L. L.; Reid, D. H. Synthesis 1993, 870.
46. (b) Zhao, H. R.; Ruan, M. D.; Fan, W. Q.; Zhou, X. J. Synth. Commun. 1994, 24, 1761.