New synthetic technology for the rapid construction of novel heterocycles - Part 2. The reaction of IBX with anilides and related compounds

Angewandte Chemie - International Edition

Volumn 39, Issue 3, 2000, Pages 625-628

  Nicolaou, K C ^a   Zhong, Yong Li ^a   Baran, Phil S ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

Domino reactions; Heterocycles; Hypervalent compounds; Iodine reagents; Synthetic methods

Indexed keywords

ANILIDE; HETEROCYCLIC COMPOUND; IODINE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; MOLECULAR MODEL; REACTION ANALYSIS; SYNTHESIS;

EID: 0034602983     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (31)

1. K. C. Nicolaou, Y.-L. Zhong, P. S. Baran, Angew. Chem. 2000, 112, 1026-1029; Angew. Chem. Int. Ed. 1999, 38, 2000, 112, 1026-1029.
2. K. C. Nicolaou, Y.-L. Zhong, P. S. Baran, Angew. Chem. 2000, 112, 1026-1029; Angew. Chem. Int. Ed. 1999, 38, 2000, 112, 1026-1029.
3. K. C. Nicolaou, Y.-L. Zhong, P. S. Baran, Angew. Chem. 2000, 112, 1026-1029; Angew. Chem. Int. Ed. 1999, 38, 2000, 112, 1026-1029.
4. First preparation of IBX: C. Hartman, V. Meyer, Ber. Dtsch. Chem. Ges. 1893, 26, 1727; for a superior route to IBX, see: M. Frigerio, M. Santagostino, S. Sputore, J. Org. Chem. 1999, 64, 4537-4538; introduction of the acronym "IBX": A. R. Katritzky, B. L. Duell, J. K. Gallos, Org. Magn. Reson. 1989, 27, 1007; use of IBX as a selective oxidant for alcohols: M. Frigerio, M. Santagostino, Tetrahedron Lett. 1994, 35, 8019-8022; E. J. Corey, A. Palani, Tetrahedron Lett. 1995, 36, 3485-3488.
5. First preparation of IBX: C. Hartman, V. Meyer, Ber. Dtsch. Chem. Ges. 1893, 26, 1727; for a superior route to IBX, see: M. Frigerio, M. Santagostino, S. Sputore, J. Org. Chem. 1999, 64, 4537-4538; introduction of the acronym "IBX": A. R. Katritzky, B. L. Duell, J. K. Gallos, Org. Magn. Reson. 1989, 27, 1007; use of IBX as a selective oxidant for alcohols: M. Frigerio, M. Santagostino, Tetrahedron Lett. 1994, 35, 8019-8022; E. J. Corey, A. Palani, Tetrahedron Lett. 1995, 36, 3485-3488.
6. First preparation of IBX: C. Hartman, V. Meyer, Ber. Dtsch. Chem. Ges. 1893, 26, 1727; for a superior route to IBX, see: M. Frigerio, M. Santagostino, S. Sputore, J. Org. Chem. 1999, 64, 4537-4538; introduction of the acronym "IBX": A. R. Katritzky, B. L. Duell, J. K. Gallos, Org. Magn. Reson. 1989, 27, 1007; use of IBX as a selective oxidant for alcohols: M. Frigerio, M. Santagostino, Tetrahedron Lett. 1994, 35, 8019-8022; E. J. Corey, A. Palani, Tetrahedron Lett. 1995, 36, 3485-3488.
7. First preparation of IBX: C. Hartman, V. Meyer, Ber. Dtsch. Chem. Ges. 1893, 26, 1727; for a superior route to IBX, see: M. Frigerio, M. Santagostino, S. Sputore, J. Org. Chem. 1999, 64, 4537-4538; introduction of the acronym "IBX": A. R. Katritzky, B. L. Duell, J. K. Gallos, Org. Magn. Reson. 1989, 27, 1007; use of IBX as a selective oxidant for alcohols: M. Frigerio, M. Santagostino, Tetrahedron Lett. 1994, 35, 8019-8022; E. J. Corey, A. Palani, Tetrahedron Lett. 1995, 36, 3485-3488.
8. First preparation of IBX: C. Hartman, V. Meyer, Ber. Dtsch. Chem. Ges. 1893, 26, 1727; for a superior route to IBX, see: M. Frigerio, M. Santagostino, S. Sputore, J. Org. Chem. 1999, 64, 4537-4538; introduction of the acronym "IBX": A. R. Katritzky, B. L. Duell, J. K. Gallos, Org. Magn. Reson. 1989, 27, 1007; use of IBX as a selective oxidant for alcohols: M. Frigerio, M. Santagostino, Tetrahedron Lett. 1994, 35, 8019-8022; E. J. Corey, A. Palani, Tetrahedron Lett. 1995, 36, 3485-3488.
9. One exception is the nitro group, in which case the reaction did not proceed under the normal conditions.
10. Crystallographic data (excluding structure factors) for the structures reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC-133867. Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK (fax: (+ 44)1223-336-033; e-mail: deposit@ccdc.cam.ac.uk).
11. a) A.-C. Callier, B. Quiclet-Sire, S. Z. Zard, Tetrahedron Lett. 1994, 35, 6109-6112;
12. b) A.-C. Callier, B. Quiclet-Sire, S. Z. Zard, Tetrahedron Lett. 1995, 36, 8791-8794;
13. c) M. Newcomb, J. L. Esker, Tetrahedron Lett. 1991, 32, 1035-1038;
14. d) M. Newcomb, J. L. Esker, Tetrahedron Lett. 1993, 34, 6877-6880;
15. e) A. J. Clark, J. L. Peacock, Tetrahedron Lett. 1998, 39, 6029-6032;
16. f) A. J. Clark, R. P. Filik, J. L. Peacock, G. H. Thomas, Synlett 1999, 441-443;
17. g) A. J. Clark, R. J. Deeth, C. J. Samuel, H. Wongtap, Synlett 1999, 444-446.
18. S. De Munari, M. Frigerio, M. Santagostino, J. Org. Chem. 1996, 61, 9272-9279; M. Frigerio, M. Santagostino, S. Sputore, G. Palmisano, J. Org. Chem. 1995, 60, 7272-7276.
19. S. De Munari, M. Frigerio, M. Santagostino, J. Org. Chem. 1996, 61, 9272-9279; M. Frigerio, M. Santagostino, S. Sputore, G. Palmisano, J. Org. Chem. 1995, 60, 7272-7276.
20. 6]DMSO at varying temperatures (25-110 C) in an NMR tube. No intermediates could be detected; only product formation and some decomposition of IBX was observed.
21. B. B. Snider, Chem. Rev. 1996, 96, 339-363.
22. [1] also requires anilides as substrates.
23. A literature search using SciFinder (ACS) to probe the popularity of these structural types in natural products and medicinally important compounds led to over 50 000 hits. The potential that these functionalities have for further elaboration to other scaffolds is nearly infinite. The following are some selected examples. Natural products: Yunnaneic acids A-D, uremic toxin-decreasing effects: T. Takashi, A. Nishimura, I. Kouno, G.-I. Nonaka, T.-J. Young, J. Nat. Prod. 1996, 59, 843-849; isoschizogamine, HIV inhibitor: J. Hajicek, J. Taimr, M. Budesinsky, Tetrahedron Lett. 1998, 39, 505-508; G. T. Tan, J. M. Pezzuoto, A. D. Kinghorn, S. H. Hughes, J. Nat. Prod. 1991, 54, 143- 154. Medicinally important compounds: a) Therapeutic CNS agents: M. Varasi, F. Heidempergher, C. Caccia, P. Salvati (Pharmacia S.p.A., Italy), WO-A 95-EP1650; b) 5-HT3 antagonists: M. Varasi, F. Heidempergher, C. Arrigoni, C. Caccia (Farmitalis Carlo Erba S.R.L., Italy), WO-A 93-EP1498; c) antihyperlipidemics: S. Yano, T. Ohno, K. Ogawa, H. Yamada, T. Shirasaka, H. Kawamura, S. Watanabe (Taiho Pharmaceutical Co., Ltd., Japan), WO-A 930JP559; d) hypolipemics and hypoglycemics: II. Yanagisawa, K. Fujimoto, T. Fujita, K. Wada, M. Oguchi, T. Yoshioka, T. Fujiwara, H. Horikoshi (Sankyo Co., Japan) JP-A 95-162442; e) monoamine oxidase inhibitors: C. Banzati, A. Della Torre, P. Melloni, D. Pieraccioli, P. Salvadori, J. Heterocycl. Chem. 1983, 20, 139-140; f) antidepressants: (Erba, Carlo S.p.A., Italy) IT-B 75-30829.
24. A literature search using SciFinder (ACS) to probe the popularity of these structural types in natural products and medicinally important compounds led to over 50 000 hits. The potential that these functionalities have for further elaboration to other scaffolds is nearly infinite. The following are some selected examples. Natural products: Yunnaneic acids A-D, uremic toxin-decreasing effects: T. Takashi, A. Nishimura, I. Kouno, G.-I. Nonaka, T.-J. Young, J. Nat. Prod. 1996, 59, 843-849; isoschizogamine, HIV inhibitor: J. Hajicek, J. Taimr, M. Budesinsky, Tetrahedron Lett. 1998, 39, 505-508; G. T. Tan, J. M. Pezzuoto, A. D. Kinghorn, S. H. Hughes, J. Nat. Prod. 1991, 54, 143- 154. Medicinally important compounds: a) Therapeutic CNS agents: M. Varasi, F. Heidempergher, C. Caccia, P. Salvati (Pharmacia S.p.A., Italy), WO-A 95-EP1650; b) 5-HT3 antagonists: M. Varasi, F. Heidempergher, C. Arrigoni, C. Caccia (Farmitalis Carlo Erba S.R.L., Italy), WO-A 93-EP1498; c) antihyperlipidemics: S. Yano, T. Ohno, K. Ogawa, H. Yamada, T. Shirasaka, H. Kawamura, S. Watanabe (Taiho Pharmaceutical Co., Ltd., Japan), WO-A 930JP559; d) hypolipemics and hypoglycemics: II. Yanagisawa, K. Fujimoto, T. Fujita, K. Wada, M. Oguchi, T. Yoshioka, T. Fujiwara, H. Horikoshi (Sankyo Co., Japan) JP-A 95-162442; e) monoamine oxidase inhibitors: C. Banzati, A. Della Torre, P. Melloni, D. Pieraccioli, P. Salvadori, J. Heterocycl. Chem. 1983, 20, 139-140; f) antidepressants: (Erba, Carlo S.p.A., Italy) IT-B 75-30829.
25. A literature search using SciFinder (ACS) to probe the popularity of these structural types in natural products and medicinally important compounds led to over 50 000 hits. The potential that these functionalities have for further elaboration to other scaffolds is nearly infinite. The following are some selected examples. Natural products: Yunnaneic acids A-D, uremic toxin-decreasing effects: T. Takashi, A. Nishimura, I. Kouno, G.-I. Nonaka, T.-J. Young, J. Nat. Prod. 1996, 59, 843-849; isoschizogamine, HIV inhibitor: J. Hajicek, J. Taimr, M. Budesinsky, Tetrahedron Lett. 1998, 39, 505-508; G. T. Tan, J. M. Pezzuoto, A. D. Kinghorn, S. H. Hughes, J. Nat. Prod. 1991, 54, 143-154. Medicinally important compounds: a) Therapeutic CNS agents: M. Varasi, F. Heidempergher, C. Caccia, P. Salvati (Pharmacia S.p.A., Italy), WO-A 95-EP1650; b) 5-HT3 antagonists: M. Varasi, F. Heidempergher, C. Arrigoni, C. Caccia (Farmitalis Carlo Erba S.R.L., Italy), WO-A 93-EP1498; c) antihyperlipidemics: S. Yano, T. Ohno, K. Ogawa, H. Yamada, T. Shirasaka, H. Kawamura, S. Watanabe (Taiho Pharmaceutical Co., Ltd., Japan), WO-A 930JP559; d) hypolipemics and hypoglycemics: II. Yanagisawa, K. Fujimoto, T. Fujita, K. Wada, M. Oguchi, T. Yoshioka, T. Fujiwara, H. Horikoshi (Sankyo Co., Japan) JP-A 95-162442; e) monoamine oxidase inhibitors: C. Banzati, A. Della Torre, P. Melloni, D. Pieraccioli, P. Salvadori, J. Heterocycl. Chem. 1983, 20, 139-140; f) antidepressants: (Erba, Carlo S.p.A., Italy) IT-B 75-30829.
26. A literature search using SciFinder (ACS) to probe the popularity of these structural types in natural products and medicinally important compounds led to over 50 000 hits. The potential that these functionalities have for further elaboration to other scaffolds is nearly infinite. The following are some selected examples. Natural products: Yunnaneic acids A-D, uremic toxin-decreasing effects: T. Takashi, A. Nishimura, I. Kouno, G.-I. Nonaka, T.-J. Young, J. Nat. Prod. 1996, 59, 843-849; isoschizogamine, HIV inhibitor: J. Hajicek, J. Taimr, M. Budesinsky, Tetrahedron Lett. 1998, 39, 505-508; G. T. Tan, J. M. Pezzuoto, A. D. Kinghorn, S. H. Hughes, J. Nat. Prod. 1991, 54, 143- 154. Medicinally important compounds: a) Therapeutic CNS agents: M. Varasi, F. Heidempergher, C. Caccia, P. Salvati (Pharmacia S.p.A., Italy), WO-A 95-EP1650; b) 5-HT3 antagonists: M. Varasi, F. Heidempergher, C. Arrigoni, C. Caccia (Farmitalis Carlo Erba S.R.L., Italy), WO-A 93-EP1498; c) antihyperlipidemics: S. Yano, T. Ohno, K. Ogawa, H. Yamada, T. Shirasaka, H. Kawamura, S. Watanabe (Taiho Pharmaceutical Co., Ltd., Japan), WO-A 930JP559; d) hypolipemics and hypoglycemics: II. Yanagisawa, K. Fujimoto, T. Fujita, K. Wada, M. Oguchi, T. Yoshioka, T. Fujiwara, H. Horikoshi (Sankyo Co., Japan) JP-A 95-162442; e) monoamine oxidase inhibitors: C. Banzati, A. Della Torre, P. Melloni, D. Pieraccioli, P. Salvadori, J. Heterocycl. Chem. 1983, 20, 139-140; f) antidepressants: (Erba, Carlo S.p.A., Italy) IT-B 75-30829.
27. A literature search using SciFinder (ACS) to probe the popularity of these structural types in natural products and medicinally important compounds led to over 50 000 hits. The potential that these functionalities have for further elaboration to other scaffolds is nearly infinite. The following are some selected examples. Natural products: Yunnaneic acids A-D, uremic toxin-decreasing effects: T. Takashi, A. Nishimura, I. Kouno, G.-I. Nonaka, T.-J. Young, J. Nat. Prod. 1996, 59, 843-849; isoschizogamine, HIV inhibitor: J. Hajicek, J. Taimr, M. Budesinsky, Tetrahedron Lett. 1998, 39, 505-508; G. T. Tan, J. M. Pezzuoto, A. D. Kinghorn, S. H. Hughes, J. Nat. Prod. 1991, 54, 143- 154. Medicinally important compounds: a) Therapeutic CNS agents: M. Varasi, F. Heidempergher, C. Caccia, P. Salvati (Pharmacia S.p.A., Italy), WO-A 95-EP1650; b) 5-HT3 antagonists: M. Varasi, F. Heidempergher, C. Arrigoni, C. Caccia (Farmitalis Carlo Erba S.R.L., Italy), WO-A 93-EP1498; c) antihyperlipidemics: S. Yano, T. Ohno, K. Ogawa, H. Yamada, T. Shirasaka, H. Kawamura, S. Watanabe (Taiho Pharmaceutical Co., Ltd., Japan), WO-A 930JP559; d) hypolipemics and hypoglycemics: II. Yanagisawa, K. Fujimoto, T. Fujita, K. Wada, M. Oguchi, T. Yoshioka, T. Fujiwara, H. Horikoshi (Sankyo Co., Japan) JP-A 95-162442; e) monoamine oxidase inhibitors: C. Banzati, A. Della Torre, P. Melloni, D. Pieraccioli, P. Salvadori, J. Heterocycl. Chem. 1983, 20, 139-140; f) antidepressants: (Erba, Carlo S.p.A., Italy) IT-B 75-30829.
28. A literature search using SciFinder (ACS) to probe the popularity of these structural types in natural products and medicinally important compounds led to over 50 000 hits. The potential that these functionalities have for further elaboration to other scaffolds is nearly infinite. The following are some selected examples. Natural products: Yunnaneic acids A-D, uremic toxin-decreasing effects: T. Takashi, A. Nishimura, I. Kouno, G.-I. Nonaka, T.-J. Young, J. Nat. Prod. 1996, 59, 843-849; isoschizogamine, HIV inhibitor: J. Hajicek, J. Taimr, M. Budesinsky, Tetrahedron Lett. 1998, 39, 505-508; G. T. Tan, J. M. Pezzuoto, A. D. Kinghorn, S. H. Hughes, J. Nat. Prod. 1991, 54, 143- 154. Medicinally important compounds: a) Therapeutic CNS agents: M. Varasi, F. Heidempergher, C. Caccia, P. Salvati (Pharmacia S.p.A., Italy), WO-A 95-EP1650; b) 5-HT3 antagonists: M. Varasi, F. Heidempergher, C. Arrigoni, C. Caccia (Farmitalis Carlo Erba S.R.L., Italy), WO-A 93-EP1498; c) antihyperlipidemics: S. Yano, T. Ohno, K. Ogawa, H. Yamada, T. Shirasaka, H. Kawamura, S. Watanabe (Taiho Pharmaceutical Co., Ltd., Japan), WO-A 930JP559; d) hypolipemics and hypoglycemics: II. Yanagisawa, K. Fujimoto, T. Fujita, K. Wada, M. Oguchi, T. Yoshioka, T. Fujiwara, H. Horikoshi (Sankyo Co., Japan) JP-A 95-162442; e) monoamine oxidase inhibitors: C. Banzati, A. Della Torre, P. Melloni, D. Pieraccioli, P. Salvadori, J. Heterocycl. Chem. 1983, 20, 139-140; f) antidepressants: (Erba, Carlo S.p.A., Italy) IT-B 75-30829.
29. A literature search using SciFinder (ACS) to probe the popularity of these structural types in natural products and medicinally important compounds led to over 50 000 hits. The potential that these functionalities have for further elaboration to other scaffolds is nearly infinite. The following are some selected examples. Natural products: Yunnaneic acids A-D, uremic toxin-decreasing effects: T. Takashi, A. Nishimura, I. Kouno, G.-I. Nonaka, T.-J. Young, J. Nat. Prod. 1996, 59, 843-849; isoschizogamine, HIV inhibitor: J. Hajicek, J. Taimr, M. Budesinsky, Tetrahedron Lett. 1998, 39, 505-508; G. T. Tan, J. M. Pezzuoto, A. D. Kinghorn, S. H. Hughes, J. Nat. Prod. 1991, 54, 143- 154. Medicinally important compounds: a) Therapeutic CNS agents: M. Varasi, F. Heidempergher, C. Caccia, P. Salvati (Pharmacia S.p.A., Italy), WO-A 95-EP1650; b) 5-HT3 antagonists: M. Varasi, F. Heidempergher, C. Arrigoni, C. Caccia (Farmitalis Carlo Erba S.R.L., Italy), WO-A 93-EP1498; c) antihyperlipidemics: S. Yano, T. Ohno, K. Ogawa, H. Yamada, T. Shirasaka, H. Kawamura, S. Watanabe (Taiho Pharmaceutical Co., Ltd., Japan), WO-A 930JP559; d) hypolipemics and hypoglycemics: II. Yanagisawa, K. Fujimoto, T. Fujita, K. Wada, M. Oguchi, T. Yoshioka, T. Fujiwara, H. Horikoshi (Sankyo Co., Japan) JP-A 95-162442; e) monoamine oxidase inhibitors: C. Banzati, A. Della Torre, P. Melloni, D. Pieraccioli, P. Salvadori, J. Heterocycl. Chem. 1983, 20, 139-140; f) antidepressants: (Erba, Carlo S.p.A., Italy) IT-B 75-30829.
30. A literature search using SciFinder (ACS) to probe the popularity of these structural types in natural products and medicinally important compounds led to over 50 000 hits. The potential that these functionalities have for further elaboration to other scaffolds is nearly infinite. The following are some selected examples. Natural products: Yunnaneic acids A-D, uremic toxin-decreasing effects: T. Takashi, A. Nishimura, I. Kouno, G.-I. Nonaka, T.-J. Young, J. Nat. Prod. 1996, 59, 843-849; isoschizogamine, HIV inhibitor: J. Hajicek, J. Taimr, M. Budesinsky, Tetrahedron Lett. 1998, 39, 505-508; G. T. Tan, J. M. Pezzuoto, A. D. Kinghorn, S. H. Hughes, J. Nat. Prod. 1991, 54, 143- 154. Medicinally important compounds: a) Therapeutic CNS agents: M. Varasi, F. Heidempergher, C. Caccia, P. Salvati (Pharmacia S.p.A., Italy), WO-A 95-EP1650; b) 5-HT3 antagonists: M. Varasi, F. Heidempergher, C. Arrigoni, C. Caccia (Farmitalis Carlo Erba S.R.L., Italy), WO-A 93-EP1498; c) antihyperlipidemics: S. Yano, T. Ohno, K. Ogawa, H. Yamada, T. Shirasaka, H. Kawamura, S. Watanabe (Taiho Pharmaceutical Co., Ltd., Japan), WO-A 930JP559; d) hypolipemics and hypoglycemics: II. Yanagisawa, K. Fujimoto, T. Fujita, K. Wada, M. Oguchi, T. Yoshioka, T. Fujiwara, H. Horikoshi (Sankyo Co., Japan) JP-A 95-162442; e) monoamine oxidase inhibitors: C. Banzati, A. Della Torre, P. Melloni, D. Pieraccioli, P. Salvadori, J. Heterocycl. Chem. 1983, 20, 139-140; f) antidepressants: (Erba, Carlo S.p.A., Italy) IT-B 75-30829.
31. A literature search using SciFinder (ACS) to probe the popularity of these structural types in natural products and medicinally important compounds led to over 50 000 hits. The potential that these functionalities have for further elaboration to other scaffolds is nearly infinite. The following are some selected examples. Natural products: Yunnaneic acids A-D, uremic toxin-decreasing effects: T. Takashi, A. Nishimura, I. Kouno, G.-I. Nonaka, T.-J. Young, J. Nat. Prod. 1996, 59, 843-849; isoschizogamine, HIV inhibitor: J. Hajicek, J. Taimr, M. Budesinsky, Tetrahedron Lett. 1998, 39, 505-508; G. T. Tan, J. M. Pezzuoto, A. D. Kinghorn, S. H. Hughes, J. Nat. Prod. 1991, 54, 143- 154. Medicinally important compounds: a) Therapeutic CNS agents: M. Varasi, F. Heidempergher, C. Caccia, P. Salvati (Pharmacia S.p.A., Italy), WO-A 95-EP1650; b) 5-HT3 antagonists: M. Varasi, F. Heidempergher, C. Arrigoni, C. Caccia (Farmitalis Carlo Erba S.R.L., Italy), WO-A 93-EP1498; c) antihyperlipidemics: S. Yano, T. Ohno, K. Ogawa, H. Yamada, T. Shirasaka, H. Kawamura, S. Watanabe (Taiho Pharmaceutical Co., Ltd., Japan), WO-A 930JP559; d) hypolipemics and hypoglycemics: II. Yanagisawa, K. Fujimoto, T. Fujita, K. Wada, M. Oguchi, T. Yoshioka, T. Fujiwara, H. Horikoshi (Sankyo Co., Japan) JP-A 95-162442; e) monoamine oxidase inhibitors: C. Banzati, A. Della Torre, P. Melloni, D. Pieraccioli, P. Salvadori, J. Heterocycl. Chem. 1983, 20, 139-140; f) antidepressants: (Erba, Carlo S.p.A., Italy) IT-B 75-30829.