SCOPUS 정보 검색 플랫폼

Tetrahedron Letters

Volumn 43, Issue 36, 2002, Pages 6309-6311

A new type of amide formation from thiocarboxylic acid and alkyl azide

(3) Park, Sang Don a Oh, Jung Hee a Lim, Dongyeol a

a Sejong University (South Korea)

Author keywords

Amide; Azide; Phosphine; Staudinger intermediate; Thiocarboxylic acid

Indexed keywords

AMIDE; AZIDE; CARBOXYLIC ACID DERIVATIVE; PHOSPHINE DERIVATIVE; THIOCARBOXYLIC ACID; UNCLASSIFIED DRUG;

AMIDATION; ARTICLE; CHEMICAL BINDING; REACTION ANALYSIS;

EID: 0037009699 PISSN: 00404039 EISSN: None Source Type: Journal
DOI: 10.1016/S0040-4039(02)01397-7 Document Type: Article

Times cited : (14)

References (23)

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5
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6
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- Bosch, I.¹ Romea, P.² Urpi, F.³ Vilarrasa, J.⁴

7
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8
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- For selected examples, see: (a) Garcia, J.; Urpi, F.; Vilarrasa, J. Tetrahedron Lett. 1984, 25, 4841-4844; (b) Garcia, J.; Vilarrasa, J. Tetrahedron Lett. 1984, 27, 639-640; (c) Urpi, F.; Vilarrasa, J. Tetrahedron Lett. 1986, 27, 4623-4624; (d) Bosch, I.; Romea, P.; Urpi, F.; Vilarrasa, J. Tetrahedron Lett. 1993, 34, 4671-4674; (e) Inazu, T.; Kobayashi, K. Synlett 1993, 869-870; (f) Bosch, I.; Urpi, F.; Vilarrasa, J. J. Chem. Soc., Chem. Commun. 1995, 91-92; (g) Shalev, D. E.; Chiacchiera, S. M.; Radkowsky, A. E.; Kosower, E. M. J. Org. Chem. 1996, 61, 1689-1701; (h) Bosch, I.; Gonzalez, A.; Urpi, F.; Vilarrasa, J. J. Org. Chem. 1996, 61, 5638-5643; (i) Tang, Z.; Pelletier, J. C. Tetrahedron Lett. 1998, 39, 4773-4776; (j) Ariza, X.; Urpi, F.; Viladomat, C.; Vilarrasa, J. Tetrahedron Lett. 1998, 39, 9101-9102; (k) Mizuno, M.; Muramoto, I.; Kobayashi, K.; Yaginuma, H.; Inazu, T. Synthesis-Stuttgart 1999, 162-165; (l) Mizuno, M.; Haneda, K.; Iguchi, R.; Muramoto, I.; Kawakami, T.; Aimoto, S.; Yamamoto, K.; Inazu, T. J. Am. Chem. Soc. 1999, 121, 284-290; (m) Boullanger, P.; Maunier, V.; Lafont, D. Carbohydr. Res. 2000, 324, 97-106; (n) Malkinson, J. P.; Falconer, R. A.; Toth, I. J. Org. Chem. 2000, 65, 5249-5252.
- (1995) J. Chem. Soc., Chem. Commun. , pp. 91-92
- Bosch, I.¹ Urpi, F.² Vilarrasa, J.³

9
- 0001399558
- For selected examples, see: (a) Garcia, J.; Urpi, F.; Vilarrasa, J. Tetrahedron Lett. 1984, 25, 4841-4844; (b) Garcia, J.; Vilarrasa, J. Tetrahedron Lett. 1984, 27, 639-640; (c) Urpi, F.; Vilarrasa, J. Tetrahedron Lett. 1986, 27, 4623-4624; (d) Bosch, I.; Romea, P.; Urpi, F.; Vilarrasa, J. Tetrahedron Lett. 1993, 34, 4671-4674; (e) Inazu, T.; Kobayashi, K. Synlett 1993, 869-870; (f) Bosch, I.; Urpi, F.; Vilarrasa, J. J. Chem. Soc., Chem. Commun. 1995, 91-92; (g) Shalev, D. E.; Chiacchiera, S. M.; Radkowsky, A. E.; Kosower, E. M. J. Org. Chem. 1996, 61, 1689-1701; (h) Bosch, I.; Gonzalez, A.; Urpi, F.; Vilarrasa, J. J. Org. Chem. 1996, 61, 5638-5643; (i) Tang, Z.; Pelletier, J. C. Tetrahedron Lett. 1998, 39, 4773-4776; (j) Ariza, X.; Urpi, F.; Viladomat, C.; Vilarrasa, J. Tetrahedron Lett. 1998, 39, 9101-9102; (k) Mizuno, M.; Muramoto, I.; Kobayashi, K.; Yaginuma, H.; Inazu, T. Synthesis-Stuttgart 1999, 162-165; (l) Mizuno, M.; Haneda, K.; Iguchi, R.; Muramoto, I.; Kawakami, T.; Aimoto, S.; Yamamoto, K.; Inazu, T. J. Am. Chem. Soc. 1999, 121, 284-290; (m) Boullanger, P.; Maunier, V.; Lafont, D. Carbohydr. Res. 2000, 324, 97-106; (n) Malkinson, J. P.; Falconer, R. A.; Toth, I. J. Org. Chem. 2000, 65, 5249-5252.
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- Shalev, D.E.¹ Chiacchiera, S.M.² Radkowsky, A.E.³ Kosower, E.M.⁴

10
- 0001536803
- For selected examples, see: (a) Garcia, J.; Urpi, F.; Vilarrasa, J. Tetrahedron Lett. 1984, 25, 4841-4844; (b) Garcia, J.; Vilarrasa, J. Tetrahedron Lett. 1984, 27, 639-640; (c) Urpi, F.; Vilarrasa, J. Tetrahedron Lett. 1986, 27, 4623-4624; (d) Bosch, I.; Romea, P.; Urpi, F.; Vilarrasa, J. Tetrahedron Lett. 1993, 34, 4671-4674; (e) Inazu, T.; Kobayashi, K. Synlett 1993, 869-870; (f) Bosch, I.; Urpi, F.; Vilarrasa, J. J. Chem. Soc., Chem. Commun. 1995, 91-92; (g) Shalev, D. E.; Chiacchiera, S. M.; Radkowsky, A. E.; Kosower, E. M. J. Org. Chem. 1996, 61, 1689-1701; (h) Bosch, I.; Gonzalez, A.; Urpi, F.; Vilarrasa, J. J. Org. Chem. 1996, 61, 5638-5643; (i) Tang, Z.; Pelletier, J. C. Tetrahedron Lett. 1998, 39, 4773-4776; (j) Ariza, X.; Urpi, F.; Viladomat, C.; Vilarrasa, J. Tetrahedron Lett. 1998, 39, 9101-9102; (k) Mizuno, M.; Muramoto, I.; Kobayashi, K.; Yaginuma, H.; Inazu, T. Synthesis-Stuttgart 1999, 162-165; (l) Mizuno, M.; Haneda, K.; Iguchi, R.; Muramoto, I.; Kawakami, T.; Aimoto, S.; Yamamoto, K.; Inazu, T. J. Am. Chem. Soc. 1999, 121, 284-290; (m) Boullanger, P.; Maunier, V.; Lafont, D. Carbohydr. Res. 2000, 324, 97-106; (n) Malkinson, J. P.; Falconer, R. A.; Toth, I. J. Org. Chem. 2000, 65, 5249-5252.
- (1996) J. Org. Chem. , vol.61 , pp. 5638-5643
- Bosch, I.¹ Gonzalez, A.² Urpi, F.³ Vilarrasa, J.⁴

11
- 0032474786
- For selected examples, see: (a) Garcia, J.; Urpi, F.; Vilarrasa, J. Tetrahedron Lett. 1984, 25, 4841-4844; (b) Garcia, J.; Vilarrasa, J. Tetrahedron Lett. 1984, 27, 639-640; (c) Urpi, F.; Vilarrasa, J. Tetrahedron Lett. 1986, 27, 4623-4624; (d) Bosch, I.; Romea, P.; Urpi, F.; Vilarrasa, J. Tetrahedron Lett. 1993, 34, 4671-4674; (e) Inazu, T.; Kobayashi, K. Synlett 1993, 869-870; (f) Bosch, I.; Urpi, F.; Vilarrasa, J. J. Chem. Soc., Chem. Commun. 1995, 91-92; (g) Shalev, D. E.; Chiacchiera, S. M.; Radkowsky, A. E.; Kosower, E. M. J. Org. Chem. 1996, 61, 1689-1701; (h) Bosch, I.; Gonzalez, A.; Urpi, F.; Vilarrasa, J. J. Org. Chem. 1996, 61, 5638-5643; (i) Tang, Z.; Pelletier, J. C. Tetrahedron Lett. 1998, 39, 4773-4776; (j) Ariza, X.; Urpi, F.; Viladomat, C.; Vilarrasa, J. Tetrahedron Lett. 1998, 39, 9101-9102; (k) Mizuno, M.; Muramoto, I.; Kobayashi, K.; Yaginuma, H.; Inazu, T. Synthesis-Stuttgart 1999, 162-165; (l) Mizuno, M.; Haneda, K.; Iguchi, R.; Muramoto, I.; Kawakami, T.; Aimoto, S.; Yamamoto, K.; Inazu, T. J. Am. Chem. Soc. 1999, 121, 284-290; (m) Boullanger, P.; Maunier, V.; Lafont, D. Carbohydr. Res. 2000, 324, 97-106; (n) Malkinson, J. P.; Falconer, R. A.; Toth, I. J. Org. Chem. 2000, 65, 5249-5252.
- (1998) Tetrahedron Lett. , vol.39 , pp. 4773-4776
- Tang, Z.¹ Pelletier, J.C.²

12
- 0032481022
- For selected examples, see: (a) Garcia, J.; Urpi, F.; Vilarrasa, J. Tetrahedron Lett. 1984, 25, 4841-4844; (b) Garcia, J.; Vilarrasa, J. Tetrahedron Lett. 1984, 27, 639-640; (c) Urpi, F.; Vilarrasa, J. Tetrahedron Lett. 1986, 27, 4623-4624; (d) Bosch, I.; Romea, P.; Urpi, F.; Vilarrasa, J. Tetrahedron Lett. 1993, 34, 4671-4674; (e) Inazu, T.; Kobayashi, K. Synlett 1993, 869-870; (f) Bosch, I.; Urpi, F.; Vilarrasa, J. J. Chem. Soc., Chem. Commun. 1995, 91-92; (g) Shalev, D. E.; Chiacchiera, S. M.; Radkowsky, A. E.; Kosower, E. M. J. Org. Chem. 1996, 61, 1689-1701; (h) Bosch, I.; Gonzalez, A.; Urpi, F.; Vilarrasa, J. J. Org. Chem. 1996, 61, 5638-5643; (i) Tang, Z.; Pelletier, J. C. Tetrahedron Lett. 1998, 39, 4773-4776; (j) Ariza, X.; Urpi, F.; Viladomat, C.; Vilarrasa, J. Tetrahedron Lett. 1998, 39, 9101-9102; (k) Mizuno, M.; Muramoto, I.; Kobayashi, K.; Yaginuma, H.; Inazu, T. Synthesis-Stuttgart 1999, 162-165; (l) Mizuno, M.; Haneda, K.; Iguchi, R.; Muramoto, I.; Kawakami, T.; Aimoto, S.; Yamamoto, K.; Inazu, T. J. Am. Chem. Soc. 1999, 121, 284-290; (m) Boullanger, P.; Maunier, V.; Lafont, D. Carbohydr. Res. 2000, 324, 97-106; (n) Malkinson, J. P.; Falconer, R. A.; Toth, I. J. Org. Chem. 2000, 65, 5249-5252.
- (1998) Tetrahedron Lett. , vol.39 , pp. 9101-9102
- Ariza, X.¹ Urpi, F.² Viladomat, C.³ Vilarrasa, J.⁴

13
- 0032960774
- For selected examples, see: (a) Garcia, J.; Urpi, F.; Vilarrasa, J. Tetrahedron Lett. 1984, 25, 4841-4844; (b) Garcia, J.; Vilarrasa, J. Tetrahedron Lett. 1984, 27, 639-640; (c) Urpi, F.; Vilarrasa, J. Tetrahedron Lett. 1986, 27, 4623-4624; (d) Bosch, I.; Romea, P.; Urpi, F.; Vilarrasa, J. Tetrahedron Lett. 1993, 34, 4671-4674; (e) Inazu, T.; Kobayashi, K. Synlett 1993, 869-870; (f) Bosch, I.; Urpi, F.; Vilarrasa, J. J. Chem. Soc., Chem. Commun. 1995, 91-92; (g) Shalev, D. E.; Chiacchiera, S. M.; Radkowsky, A. E.; Kosower, E. M. J. Org. Chem. 1996, 61, 1689-1701; (h) Bosch, I.; Gonzalez, A.; Urpi, F.; Vilarrasa, J. J. Org. Chem. 1996, 61, 5638-5643; (i) Tang, Z.; Pelletier, J. C. Tetrahedron Lett. 1998, 39, 4773-4776; (j) Ariza, X.; Urpi, F.; Viladomat, C.; Vilarrasa, J. Tetrahedron Lett. 1998, 39, 9101-9102; (k) Mizuno, M.; Muramoto, I.; Kobayashi, K.; Yaginuma, H.; Inazu, T. Synthesis-Stuttgart 1999, 162-165; (l) Mizuno, M.; Haneda, K.; Iguchi, R.; Muramoto, I.; Kawakami, T.; Aimoto, S.; Yamamoto, K.; Inazu, T. J. Am. Chem. Soc. 1999, 121, 284-290; (m) Boullanger, P.; Maunier, V.; Lafont, D. Carbohydr. Res. 2000, 324, 97-106; (n) Malkinson, J. P.; Falconer, R. A.; Toth, I. J. Org. Chem. 2000, 65, 5249-5252.
- (1999) Synthesis-Stuttgart , pp. 162-165
- Mizuno, M.¹ Muramoto, I.² Kobayashi, K.³ Yaginuma, H.⁴ Inazu, T.⁵

14
- 0033585615
- For selected examples, see: (a) Garcia, J.; Urpi, F.; Vilarrasa, J. Tetrahedron Lett. 1984, 25, 4841-4844; (b) Garcia, J.; Vilarrasa, J. Tetrahedron Lett. 1984, 27, 639-640; (c) Urpi, F.; Vilarrasa, J. Tetrahedron Lett. 1986, 27, 4623-4624; (d) Bosch, I.; Romea, P.; Urpi, F.; Vilarrasa, J. Tetrahedron Lett. 1993, 34, 4671-4674; (e) Inazu, T.; Kobayashi, K. Synlett 1993, 869-870; (f) Bosch, I.; Urpi, F.; Vilarrasa, J. J. Chem. Soc., Chem. Commun. 1995, 91-92; (g) Shalev, D. E.; Chiacchiera, S. M.; Radkowsky, A. E.; Kosower, E. M. J. Org. Chem. 1996, 61, 1689-1701; (h) Bosch, I.; Gonzalez, A.; Urpi, F.; Vilarrasa, J. J. Org. Chem. 1996, 61, 5638-5643; (i) Tang, Z.; Pelletier, J. C. Tetrahedron Lett. 1998, 39, 4773-4776; (j) Ariza, X.; Urpi, F.; Viladomat, C.; Vilarrasa, J. Tetrahedron Lett. 1998, 39, 9101-9102; (k) Mizuno, M.; Muramoto, I.; Kobayashi, K.; Yaginuma, H.; Inazu, T. Synthesis-Stuttgart 1999, 162-165; (l) Mizuno, M.; Haneda, K.; Iguchi, R.; Muramoto, I.; Kawakami, T.; Aimoto, S.; Yamamoto, K.; Inazu, T. J. Am. Chem. Soc. 1999, 121, 284-290; (m) Boullanger, P.; Maunier, V.; Lafont, D. Carbohydr. Res. 2000, 324, 97-106; (n) Malkinson, J. P.; Falconer, R. A.; Toth, I. J. Org. Chem. 2000, 65, 5249-5252.
- (1999) J. Am. Chem. Soc. , vol.121 , pp. 284-290
- Mizuno, M.¹ Haneda, K.² Iguchi, R.³ Muramoto, I.⁴ Kawakami, T.⁵ Aimoto, S.⁶ Yamamoto, K.⁷ Inazu, T.⁸

15
- 0033953293
- For selected examples, see: (a) Garcia, J.; Urpi, F.; Vilarrasa, J. Tetrahedron Lett. 1984, 25, 4841-4844; (b) Garcia, J.; Vilarrasa, J. Tetrahedron Lett. 1984, 27, 639-640; (c) Urpi, F.; Vilarrasa, J. Tetrahedron Lett. 1986, 27, 4623-4624; (d) Bosch, I.; Romea, P.; Urpi, F.; Vilarrasa, J. Tetrahedron Lett. 1993, 34, 4671-4674; (e) Inazu, T.; Kobayashi, K. Synlett 1993, 869-870; (f) Bosch, I.; Urpi, F.; Vilarrasa, J. J. Chem. Soc., Chem. Commun. 1995, 91-92; (g) Shalev, D. E.; Chiacchiera, S. M.; Radkowsky, A. E.; Kosower, E. M. J. Org. Chem. 1996, 61, 1689-1701; (h) Bosch, I.; Gonzalez, A.; Urpi, F.; Vilarrasa, J. J. Org. Chem. 1996, 61, 5638-5643; (i) Tang, Z.; Pelletier, J. C. Tetrahedron Lett. 1998, 39, 4773-4776; (j) Ariza, X.; Urpi, F.; Viladomat, C.; Vilarrasa, J. Tetrahedron Lett. 1998, 39, 9101-9102; (k) Mizuno, M.; Muramoto, I.; Kobayashi, K.; Yaginuma, H.; Inazu, T. Synthesis-Stuttgart 1999, 162-165; (l) Mizuno, M.; Haneda, K.; Iguchi, R.; Muramoto, I.; Kawakami, T.; Aimoto, S.; Yamamoto, K.; Inazu, T. J. Am. Chem. Soc. 1999, 121, 284-290; (m) Boullanger, P.; Maunier, V.; Lafont, D. Carbohydr. Res. 2000, 324, 97-106; (n) Malkinson, J. P.; Falconer, R. A.; Toth, I. J. Org. Chem. 2000, 65, 5249-5252.
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16
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- (2000) J. Org. Chem. , vol.65 , pp. 5249-5252
- Malkinson, J.P.¹ Falconer, R.A.² Toth, I.³

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21
- 0011073270
- 3 was moved, upon mixing with triphenylphosphine, from 4.32(s) to 4.41(s), then slowly to 3.87(s), corresponding to benzyl azide, phosphazide and phosphazene, respectively.
- 3 was moved, upon mixing with triphenylphosphine, from 4.32(s) to 4.41(s), then slowly to 3.87(s), corresponding to benzyl azide, phosphazide and phosphazene, respectively.

22
- 0011132573
- Upon addition of thiobenzoic acid to the phosphazene solution, NMR shift of 4.66 (d, J=5.7 Hz) appeared quickly.
- Upon addition of thiobenzoic acid to the phosphazene solution, NMR shift of 4.66 (d, J=5.7 Hz) appeared quickly.

23
- 0011096687
- 15NO: 211, Found: 211.
- 15NO: 211, Found: 211.

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.