Synthesis of aryl α-keto esters via the rearrangement of aryl cyanohydrin carbonate esters

Tetrahedron Letters

Volumn 44, Issue 5, 2003, Pages 1019-1021

  Thasana, Nopporn ^a,b   Prachyawarakorn, Vilailak ^a,b   Tontoolarug, Sopchok ^b   Ruchirawat, Somsak ^a,b  

^a CHULABHORN RESEARCH INSTITUTE   (Thailand)

^b MAHIDOL UNIVERSITY   (Thailand)

Author keywords

[No Author keywords available]

Indexed keywords

2 PHENYLBENZOFURAN 3 CARBOXYLIC ACID; CARBONIC ACID DERIVATIVE; CARBOXYLIC ACID DERIVATIVE; CYANOHYDRIN; ESTER DERIVATIVE; NITRILE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; SYNTHESIS;

EID: 0037467813     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(02)02725-9     Document Type: Article

References (30)

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12. For the synthesis of α-keto acid derivatives see: (a) Wasserman, H. H.; Ives, J. L. J. Org. Chem. 1985, 50, 3573-3580; (b) Creary, X.; Mehrsheikh-Mohammadi, M. E. J. Org. Chem. 1986, 51, 2664-2668; (c) Ozawa, F.; Kawasaki, N.; Yamamoto, T.; Yamamoto, A. Chem. Lett. 1985, 567-570; (d) Sakakura, T.; Yamashita, H.; Kobayashi, T.-A.; Hayashi, T.; Tanaka, M. J. Org. Chem. 1987, 52, 5733-5740; (e) Jefford, C. W.; Rossier, J.-C.; Boukouvalas, J. J. Chem. Soc., Chem. Commun. 1986, 1701-1702; (f) Bulman Page, P. C.; Rosenthal, S. Tetrahedron Lett. 1986, 27, 1947-1950; (g) Yu, S.; Saenz, J.; Srirangam, J. K. J. Org. Chem. 2002, 67, 1699-1702; (h) Kashima, C.; Shirahata, Y.; Tsukamoto, Y. Heterocycles 1998, 49, 459-464; (i) Nikalje, M. D.; Ali, I. S.; Dewkar, G. K.; Sudalai, A. Tetrahedron Lett. 2000, 41, 959-961; (j) Wong, M.-K.; Yu, C.-W.; Yuen, W.-H.; Yang, D. J. Org. Chem. 2001, 66, 3606-3609; (k) Hollwedel, F.; Koβmehl, G. Synthesis 1998, 1241-1242; (l) Zhang, G.-S.; Gong, H. Synth. Commun. 1999, 29, 3149-3153.
13. For the synthesis of α-keto acid derivatives see: (a) Wasserman, H. H.; Ives, J. L. J. Org. Chem. 1985, 50, 3573-3580; (b) Creary, X.; Mehrsheikh-Mohammadi, M. E. J. Org. Chem. 1986, 51, 2664-2668; (c) Ozawa, F.; Kawasaki, N.; Yamamoto, T.; Yamamoto, A. Chem. Lett. 1985, 567-570; (d) Sakakura, T.; Yamashita, H.; Kobayashi, T.-A.; Hayashi, T.; Tanaka, M. J. Org. Chem. 1987, 52, 5733-5740; (e) Jefford, C. W.; Rossier, J.-C.; Boukouvalas, J. J. Chem. Soc., Chem. Commun. 1986, 1701-1702; (f) Bulman Page, P. C.; Rosenthal, S. Tetrahedron Lett. 1986, 27, 1947-1950; (g) Yu, S.; Saenz, J.; Srirangam, J. K. J. Org. Chem. 2002, 67, 1699-1702; (h) Kashima, C.; Shirahata, Y.; Tsukamoto, Y. Heterocycles 1998, 49, 459-464; (i) Nikalje, M. D.; Ali, I. S.; Dewkar, G. K.; Sudalai, A. Tetrahedron Lett. 2000, 41, 959-961; (j) Wong, M.-K.; Yu, C.-W.; Yuen, W.-H.; Yang, D. J. Org. Chem. 2001, 66, 3606-3609; (k) Hollwedel, F.; Koβmehl, G. Synthesis 1998, 1241-1242; (l) Zhang, G.-S.; Gong, H. Synth. Commun. 1999, 29, 3149-3153.
14. For the synthesis of α-keto acid derivatives see: (a) Wasserman, H. H.; Ives, J. L. J. Org. Chem. 1985, 50, 3573-3580; (b) Creary, X.; Mehrsheikh-Mohammadi, M. E. J. Org. Chem. 1986, 51, 2664-2668; (c) Ozawa, F.; Kawasaki, N.; Yamamoto, T.; Yamamoto, A. Chem. Lett. 1985, 567-570; (d) Sakakura, T.; Yamashita, H.; Kobayashi, T.-A.; Hayashi, T.; Tanaka, M. J. Org. Chem. 1987, 52, 5733-5740; (e) Jefford, C. W.; Rossier, J.-C.; Boukouvalas, J. J. Chem. Soc., Chem. Commun. 1986, 1701-1702; (f) Bulman Page, P. C.; Rosenthal, S. Tetrahedron Lett. 1986, 27, 1947-1950; (g) Yu, S.; Saenz, J.; Srirangam, J. K. J. Org. Chem. 2002, 67, 1699-1702; (h) Kashima, C.; Shirahata, Y.; Tsukamoto, Y. Heterocycles 1998, 49, 459-464; (i) Nikalje, M. D.; Ali, I. S.; Dewkar, G. K.; Sudalai, A. Tetrahedron Lett. 2000, 41, 959-961; (j) Wong, M.-K.; Yu, C.-W.; Yuen, W.-H.; Yang, D. J. Org. Chem. 2001, 66, 3606-3609; (k) Hollwedel, F.; Koβmehl, G. Synthesis 1998, 1241-1242; (l) Zhang, G.-S.; Gong, H. Synth. Commun. 1999, 29, 3149-3153.
15. For the synthesis of α-keto acid derivatives see: (a) Wasserman, H. H.; Ives, J. L. J. Org. Chem. 1985, 50, 3573-3580; (b) Creary, X.; Mehrsheikh-Mohammadi, M. E. J. Org. Chem. 1986, 51, 2664-2668; (c) Ozawa, F.; Kawasaki, N.; Yamamoto, T.; Yamamoto, A. Chem. Lett. 1985, 567-570; (d) Sakakura, T.; Yamashita, H.; Kobayashi, T.-A.; Hayashi, T.; Tanaka, M. J. Org. Chem. 1987, 52, 5733-5740; (e) Jefford, C. W.; Rossier, J.-C.; Boukouvalas, J. J. Chem. Soc., Chem. Commun. 1986, 1701-1702; (f) Bulman Page, P. C.; Rosenthal, S. Tetrahedron Lett. 1986, 27, 1947-1950; (g) Yu, S.; Saenz, J.; Srirangam, J. K. J. Org. Chem. 2002, 67, 1699-1702; (h) Kashima, C.; Shirahata, Y.; Tsukamoto, Y. Heterocycles 1998, 49, 459-464; (i) Nikalje, M. D.; Ali, I. S.; Dewkar, G. K.; Sudalai, A. Tetrahedron Lett. 2000, 41, 959-961; (j) Wong, M.-K.; Yu, C.-W.; Yuen, W.-H.; Yang, D. J. Org. Chem. 2001, 66, 3606-3609; (k) Hollwedel, F.; Koβmehl, G. Synthesis 1998, 1241-1242; (l) Zhang, G.-S.; Gong, H. Synth. Commun. 1999, 29, 3149-3153.
16. For the synthesis of α-keto acid derivatives see: (a) Wasserman, H. H.; Ives, J. L. J. Org. Chem. 1985, 50, 3573-3580; (b) Creary, X.; Mehrsheikh-Mohammadi, M. E. J. Org. Chem. 1986, 51, 2664-2668; (c) Ozawa, F.; Kawasaki, N.; Yamamoto, T.; Yamamoto, A. Chem. Lett. 1985, 567-570; (d) Sakakura, T.; Yamashita, H.; Kobayashi, T.-A.; Hayashi, T.; Tanaka, M. J. Org. Chem. 1987, 52, 5733-5740; (e) Jefford, C. W.; Rossier, J.-C.; Boukouvalas, J. J. Chem. Soc., Chem. Commun. 1986, 1701-1702; (f) Bulman Page, P. C.; Rosenthal, S. Tetrahedron Lett. 1986, 27, 1947-1950; (g) Yu, S.; Saenz, J.; Srirangam, J. K. J. Org. Chem. 2002, 67, 1699-1702; (h) Kashima, C.; Shirahata, Y.; Tsukamoto, Y. Heterocycles 1998, 49, 459-464; (i) Nikalje, M. D.; Ali, I. S.; Dewkar, G. K.; Sudalai, A. Tetrahedron Lett. 2000, 41, 959-961; (j) Wong, M.-K.; Yu, C.-W.; Yuen, W.-H.; Yang, D. J. Org. Chem. 2001, 66, 3606-3609; (k) Hollwedel, F.; Koβmehl, G. Synthesis 1998, 1241-1242; (l) Zhang, G.-S.; Gong, H. Synth. Commun. 1999, 29, 3149-3153.
17. For the synthesis of α-keto acid derivatives see: (a) Wasserman, H. H.; Ives, J. L. J. Org. Chem. 1985, 50, 3573-3580; (b) Creary, X.; Mehrsheikh-Mohammadi, M. E. J. Org. Chem. 1986, 51, 2664-2668; (c) Ozawa, F.; Kawasaki, N.; Yamamoto, T.; Yamamoto, A. Chem. Lett. 1985, 567-570; (d) Sakakura, T.; Yamashita, H.; Kobayashi, T.-A.; Hayashi, T.; Tanaka, M. J. Org. Chem. 1987, 52, 5733-5740; (e) Jefford, C. W.; Rossier, J.-C.; Boukouvalas, J. J. Chem. Soc., Chem. Commun. 1986, 1701-1702; (f) Bulman Page, P. C.; Rosenthal, S. Tetrahedron Lett. 1986, 27, 1947-1950; (g) Yu, S.; Saenz, J.; Srirangam, J. K. J. Org. Chem. 2002, 67, 1699-1702; (h) Kashima, C.; Shirahata, Y.; Tsukamoto, Y. Heterocycles 1998, 49, 459-464; (i) Nikalje, M. D.; Ali, I. S.; Dewkar, G. K.; Sudalai, A. Tetrahedron Lett. 2000, 41, 959-961; (j) Wong, M.-K.; Yu, C.-W.; Yuen, W.-H.; Yang, D. J. Org. Chem. 2001, 66, 3606-3609; (k) Hollwedel, F.; Koβmehl, G. Synthesis 1998, 1241-1242; (l) Zhang, G.-S.; Gong, H. Synth. Commun. 1999, 29, 3149-3153.
18. For the synthesis of α-keto acid derivatives see: (a) Wasserman, H. H.; Ives, J. L. J. Org. Chem. 1985, 50, 3573-3580; (b) Creary, X.; Mehrsheikh-Mohammadi, M. E. J. Org. Chem. 1986, 51, 2664-2668; (c) Ozawa, F.; Kawasaki, N.; Yamamoto, T.; Yamamoto, A. Chem. Lett. 1985, 567-570; (d) Sakakura, T.; Yamashita, H.; Kobayashi, T.-A.; Hayashi, T.; Tanaka, M. J. Org. Chem. 1987, 52, 5733-5740; (e) Jefford, C. W.; Rossier, J.-C.; Boukouvalas, J. J. Chem. Soc., Chem. Commun. 1986, 1701-1702; (f) Bulman Page, P. C.; Rosenthal, S. Tetrahedron Lett. 1986, 27, 1947-1950; (g) Yu, S.; Saenz, J.; Srirangam, J. K. J. Org. Chem. 2002, 67, 1699-1702; (h) Kashima, C.; Shirahata, Y.; Tsukamoto, Y. Heterocycles 1998, 49, 459-464; (i) Nikalje, M. D.; Ali, I. S.; Dewkar, G. K.; Sudalai, A. Tetrahedron Lett. 2000, 41, 959-961; (j) Wong, M.-K.; Yu, C.-W.; Yuen, W.-H.; Yang, D. J. Org. Chem. 2001, 66, 3606-3609; (k) Hollwedel, F.; Koβmehl, G. Synthesis 1998, 1241-1242; (l) Zhang, G.-S.; Gong, H. Synth. Commun. 1999, 29, 3149-3153.
19. For the synthesis of α-keto acid derivatives see: (a) Wasserman, H. H.; Ives, J. L. J. Org. Chem. 1985, 50, 3573-3580; (b) Creary, X.; Mehrsheikh-Mohammadi, M. E. J. Org. Chem. 1986, 51, 2664-2668; (c) Ozawa, F.; Kawasaki, N.; Yamamoto, T.; Yamamoto, A. Chem. Lett. 1985, 567-570; (d) Sakakura, T.; Yamashita, H.; Kobayashi, T.-A.; Hayashi, T.; Tanaka, M. J. Org. Chem. 1987, 52, 5733-5740; (e) Jefford, C. W.; Rossier, J.-C.; Boukouvalas, J. J. Chem. Soc., Chem. Commun. 1986, 1701-1702; (f) Bulman Page, P. C.; Rosenthal, S. Tetrahedron Lett. 1986, 27, 1947-1950; (g) Yu, S.; Saenz, J.; Srirangam, J. K. J. Org. Chem. 2002, 67, 1699-1702; (h) Kashima, C.; Shirahata, Y.; Tsukamoto, Y. Heterocycles 1998, 49, 459-464; (i) Nikalje, M. D.; Ali, I. S.; Dewkar, G. K.; Sudalai, A. Tetrahedron Lett. 2000, 41, 959-961; (j) Wong, M.-K.; Yu, C.-W.; Yuen, W.-H.; Yang, D. J. Org. Chem. 2001, 66, 3606-3609; (k) Hollwedel, F.; Koβmehl, G. Synthesis 1998, 1241-1242; (l) Zhang, G.-S.; Gong, H. Synth. Commun. 1999, 29, 3149-3153.
20. For the synthesis of α-keto acid derivatives see: (a) Wasserman, H. H.; Ives, J. L. J. Org. Chem. 1985, 50, 3573-3580; (b) Creary, X.; Mehrsheikh-Mohammadi, M. E. J. Org. Chem. 1986, 51, 2664-2668; (c) Ozawa, F.; Kawasaki, N.; Yamamoto, T.; Yamamoto, A. Chem. Lett. 1985, 567-570; (d) Sakakura, T.; Yamashita, H.; Kobayashi, T.-A.; Hayashi, T.; Tanaka, M. J. Org. Chem. 1987, 52, 5733-5740; (e) Jefford, C. W.; Rossier, J.-C.; Boukouvalas, J. J. Chem. Soc., Chem. Commun. 1986, 1701-1702; (f) Bulman Page, P. C.; Rosenthal, S. Tetrahedron Lett. 1986, 27, 1947-1950; (g) Yu, S.; Saenz, J.; Srirangam, J. K. J. Org. Chem. 2002, 67, 1699-1702; (h) Kashima, C.; Shirahata, Y.; Tsukamoto, Y. Heterocycles 1998, 49, 459-464; (i) Nikalje, M. D.; Ali, I. S.; Dewkar, G. K.; Sudalai, A. Tetrahedron Lett. 2000, 41, 959-961; (j) Wong, M.-K.; Yu, C.-W.; Yuen, W.-H.; Yang, D. J. Org. Chem. 2001, 66, 3606-3609; (k) Hollwedel, F.; Koβmehl, G. Synthesis 1998, 1241-1242; (l) Zhang, G.-S.; Gong, H. Synth. Commun. 1999, 29, 3149-3153.
21. For the synthesis of α-keto acid derivatives see: (a) Wasserman, H. H.; Ives, J. L. J. Org. Chem. 1985, 50, 3573-3580; (b) Creary, X.; Mehrsheikh-Mohammadi, M. E. J. Org. Chem. 1986, 51, 2664-2668; (c) Ozawa, F.; Kawasaki, N.; Yamamoto, T.; Yamamoto, A. Chem. Lett. 1985, 567-570; (d) Sakakura, T.; Yamashita, H.; Kobayashi, T.-A.; Hayashi, T.; Tanaka, M. J. Org. Chem. 1987, 52, 5733-5740; (e) Jefford, C. W.; Rossier, J.-C.; Boukouvalas, J. J. Chem. Soc., Chem. Commun. 1986, 1701-1702; (f) Bulman Page, P. C.; Rosenthal, S. Tetrahedron Lett. 1986, 27, 1947-1950; (g) Yu, S.; Saenz, J.; Srirangam, J. K. J. Org. Chem. 2002, 67, 1699-1702; (h) Kashima, C.; Shirahata, Y.; Tsukamoto, Y. Heterocycles 1998, 49, 459-464; (i) Nikalje, M. D.; Ali, I. S.; Dewkar, G. K.; Sudalai, A. Tetrahedron Lett. 2000, 41, 959-961; (j) Wong, M.-K.; Yu, C.-W.; Yuen, W.-H.; Yang, D. J. Org. Chem. 2001, 66, 3606-3609; (k) Hollwedel, F.; Koβmehl, G. Synthesis 1998, 1241-1242; (l) Zhang, G.-S.; Gong, H. Synth. Commun. 1999, 29, 3149-3153.
22. For the synthesis of α-keto acid derivatives see: (a) Wasserman, H. H.; Ives, J. L. J. Org. Chem. 1985, 50, 3573-3580; (b) Creary, X.; Mehrsheikh-Mohammadi, M. E. J. Org. Chem. 1986, 51, 2664-2668; (c) Ozawa, F.; Kawasaki, N.; Yamamoto, T.; Yamamoto, A. Chem. Lett. 1985, 567-570; (d) Sakakura, T.; Yamashita, H.; Kobayashi, T.-A.; Hayashi, T.; Tanaka, M. J. Org. Chem. 1987, 52, 5733-5740; (e) Jefford, C. W.; Rossier, J.-C.; Boukouvalas, J. J. Chem. Soc., Chem. Commun. 1986, 1701-1702; (f) Bulman Page, P. C.; Rosenthal, S. Tetrahedron Lett. 1986, 27, 1947-1950; (g) Yu, S.; Saenz, J.; Srirangam, J. K. J. Org. Chem. 2002, 67, 1699-1702; (h) Kashima, C.; Shirahata, Y.; Tsukamoto, Y. Heterocycles 1998, 49, 459-464; (i) Nikalje, M. D.; Ali, I. S.; Dewkar, G. K.; Sudalai, A. Tetrahedron Lett. 2000, 41, 959-961; (j) Wong, M.-K.; Yu, C.-W.; Yuen, W.-H.; Yang, D. J. Org. Chem. 2001, 66, 3606-3609; (k) Hollwedel, F.; Koβmehl, G. Synthesis 1998, 1241-1242; (l) Zhang, G.-S.; Gong, H. Synth. Commun. 1999, 29, 3149-3153.
23. For the synthesis of α-keto acid derivatives see: (a) Wasserman, H. H.; Ives, J. L. J. Org. Chem. 1985, 50, 3573-3580; (b) Creary, X.; Mehrsheikh-Mohammadi, M. E. J. Org. Chem. 1986, 51, 2664-2668; (c) Ozawa, F.; Kawasaki, N.; Yamamoto, T.; Yamamoto, A. Chem. Lett. 1985, 567-570; (d) Sakakura, T.; Yamashita, H.; Kobayashi, T.-A.; Hayashi, T.; Tanaka, M. J. Org. Chem. 1987, 52, 5733-5740; (e) Jefford, C. W.; Rossier, J.-C.; Boukouvalas, J. J. Chem. Soc., Chem. Commun. 1986, 1701-1702; (f) Bulman Page, P. C.; Rosenthal, S. Tetrahedron Lett. 1986, 27, 1947-1950; (g) Yu, S.; Saenz, J.; Srirangam, J. K. J. Org. Chem. 2002, 67, 1699-1702; (h) Kashima, C.; Shirahata, Y.; Tsukamoto, Y. Heterocycles 1998, 49, 459-464; (i) Nikalje, M. D.; Ali, I. S.; Dewkar, G. K.; Sudalai, A. Tetrahedron Lett. 2000, 41, 959-961; (j) Wong, M.-K.; Yu, C.-W.; Yuen, W.-H.; Yang, D. J. Org. Chem. 2001, 66, 3606-3609; (k) Hollwedel, F.; Koβmehl, G. Synthesis 1998, 1241-1242; (l) Zhang, G.-S.; Gong, H. Synth. Commun. 1999, 29, 3149-3153.
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27. 4), and evaporated to give a yellow oil. Purification by distillation under reduced pressure yielded 2-benzyloxyphenyl cyanohydrin carbonate ester 2h (6.03 g, 78%).
28. 4: 311.1158. Found: 311.1159.
29. 4), and evaporated to give a yellow solid. Recrystallization using ethyl acetate and hexane yielded 2-phenylbenzofuran-3-carboxylic acid 11 (0.077 g, 65%) as yellowish crystals.
30. 3: 238.0629. Found: 238.0625.