SCOPUS 정보 검색 플랫폼

Organic Letters

Volumn 6, Issue 19, 2004, Pages 3237-3240

Demonstration of the feasibility of a direct solid-phase split-pool Biginelli synthesis of 3,4-dihydropyrimidinones

(2) Lusch, Michael J a,b Tallarico, John A a,c

a HARVARD MEDICAL SCHOOL (United States)

b MINNESOTA STATE UNIVERSITY (United States)

c NOVARTIS INSTITUTES FOR BIOMEDICAL RESEARCH (United States)

Author keywords

[No Author keywords available]

Indexed keywords

3,4 DIHYDROPYRIMIDINONE; 4 BROMOBENZALDEHYDE; 4 CHLOROBENZALDEHYDE; BENZALDEHYDE DERIVATIVE; POLYMER; POLYSTYRENE; PYRIMIDINONE DERIVATIVE; RESIN; UNCLASSIFIED DRUG; UREA;

ARTICLE; BIGINELLI REACTION; CATALYSIS; CATALYST; CHEMICAL REACTION; DRUG SYNTHESIS; REACTION ANALYSIS; TEMPERATURE SENSITIVITY;

CATALYSIS; INDICATORS AND REAGENTS; MOLECULAR STRUCTURE; PYRIMIDINONES; TEMPERATURE; UREA;

EID: 4644324512 PISSN: 15237060 EISSN: None Source Type: Journal
DOI: 10.1021/ol048946r Document Type: Article

Times cited : (56)

References (48)

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- Lindsley, C.W.¹ Chan, L.K.² Goess, B.C.³ Joseph, R.⁴ Shair, M.D.⁵

7
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- Examples of diversity-oriented synthesis: (a) [Shikimic acid library] Tan, D. S.; Foley, M. A.; Stockwell, B. R.; Shair, M. D.; Schreiber, S. L. J. Am. Chem. Soc. 1999, 121, 9073-9087. (b) [Carpanone-like library] Lindsley, C. W.; Chan, L. K.; Goess, B. C.; Joseph, R.; Shair, M. D. J. Am. Chem. Soc. 2000, 122, 422-423. (c) [Ugi/Diels-Alder/RCM library] Lee, D.; Sello, J. K.; Schreiber, S. L. Org. Lett. 2000, 2, 709-712. (d) [THOX (tetrahydrooxazepine) library] Koide, K.; Finkelstein, J. M.; Ball, Z.; Verdine, G. L. J. Am. Chem. Soc. 2001, 123, 398-408. (e) [1,3-Dioxane library] Sternson, S. M.; Louca, J. B.; Wong, J. C.; Schreiber, S. L. J. Am. Chem. Soc. 2001, 123, 1740-1747. (f) [Galanthamine library] Pelish, H. E.; Westwood, N. J.; Feng, Y.; Kirchhausen, T.; Shair, M. D. J. Am. Chem. Soc. 2001, 123, 6740-6741. (g) [Dihydropyrancarboxamide library] Stavenger, R. A.; Schreiber, S. L. Angew. Chem., Int. Ed. 2001, 40, 3417-3421. (h) [Hydroxamic acid library] Sternson, S. M.; Wong, J. C.; Grozinger, C. M.; Schreiber, S. L. Org. Lett. 2001, 3, 4239-4242. (i) [Biaryl library] Spring, D. R.; Krishnan, S.; Blackwell, H. E.; Schreiber, S. L. J. Am. Chem. Soc. 2002, 124, 1354-1363. (j) [Ferrier/Pauson-Khand library] Kubota, H.; Lim, J.; Depew, K. M.; Schreiber, S. L. Chem. Biol. 2002, 9, 265-276. (k) [Benzo[b]furan library] Liao, Y.; Reitman, M.; Zhang, Y.; Fathi, R.; Yang, Z. Org. Lett. 2002, 4, 2607-2609. (1) [Branched Diels-Alder skeletal diversity library] Kwon, O.; Park, S. B.; Schreiber, S. L. J. Am. Chem. Soc. 2002, 124, 13402-13404. (m) [Asymmetric azomethine ylide 1,3-dipolar cycloaddition library] Chen, C.; Li, X.; Schreiber, S. L. J. Am. Chem. Soc. 2003, 125, 10174-10175.
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8
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- Examples of diversity-oriented synthesis: (a) [Shikimic acid library] Tan, D. S.; Foley, M. A.; Stockwell, B. R.; Shair, M. D.; Schreiber, S. L. J. Am. Chem. Soc. 1999, 121, 9073-9087. (b) [Carpanone-like library] Lindsley, C. W.; Chan, L. K.; Goess, B. C.; Joseph, R.; Shair, M. D. J. Am. Chem. Soc. 2000, 122, 422-423. (c) [Ugi/Diels-Alder/RCM library] Lee, D.; Sello, J. K.; Schreiber, S. L. Org. Lett. 2000, 2, 709-712. (d) [THOX (tetrahydrooxazepine) library] Koide, K.; Finkelstein, J. M.; Ball, Z.; Verdine, G. L. J. Am. Chem. Soc. 2001, 123, 398-408. (e) [1,3-Dioxane library] Sternson, S. M.; Louca, J. B.; Wong, J. C.; Schreiber, S. L. J. Am. Chem. Soc. 2001, 123, 1740-1747. (f) [Galanthamine library] Pelish, H. E.; Westwood, N. J.; Feng, Y.; Kirchhausen, T.; Shair, M. D. J. Am. Chem. Soc. 2001, 123, 6740-6741. (g) [Dihydropyrancarboxamide library] Stavenger, R. A.; Schreiber, S. L. Angew. Chem., Int. Ed. 2001, 40, 3417-3421. (h) [Hydroxamic acid library] Sternson, S. M.; Wong, J. C.; Grozinger, C. M.; Schreiber, S. L. Org. Lett. 2001, 3, 4239-4242. (i) [Biaryl library] Spring, D. R.; Krishnan, S.; Blackwell, H. E.; Schreiber, S. L. J. Am. Chem. Soc. 2002, 124, 1354-1363. (j) [Ferrier/Pauson-Khand library] Kubota, H.; Lim, J.; Depew, K. M.; Schreiber, S. L. Chem. Biol. 2002, 9, 265-276. (k) [Benzo[b]furan library] Liao, Y.; Reitman, M.; Zhang, Y.; Fathi, R.; Yang, Z. Org. Lett. 2002, 4, 2607-2609. (1) [Branched Diels-Alder skeletal diversity library] Kwon, O.; Park, S. B.; Schreiber, S. L. J. Am. Chem. Soc. 2002, 124, 13402-13404. (m) [Asymmetric azomethine ylide 1,3-dipolar cycloaddition library] Chen, C.; Li, X.; Schreiber, S. L. J. Am. Chem. Soc. 2003, 125, 10174-10175.
- (2001) J. Am. Chem. Soc. , vol.123 , pp. 398-408
- Koide, K.¹ Finkelstein, J.M.² Ball, Z.³ Verdine, G.L.⁴

9
- 0035961490
- Examples of diversity-oriented synthesis: (a) [Shikimic acid library] Tan, D. S.; Foley, M. A.; Stockwell, B. R.; Shair, M. D.; Schreiber, S. L. J. Am. Chem. Soc. 1999, 121, 9073-9087. (b) [Carpanone-like library] Lindsley, C. W.; Chan, L. K.; Goess, B. C.; Joseph, R.; Shair, M. D. J. Am. Chem. Soc. 2000, 122, 422-423. (c) [Ugi/Diels-Alder/RCM library] Lee, D.; Sello, J. K.; Schreiber, S. L. Org. Lett. 2000, 2, 709-712. (d) [THOX (tetrahydrooxazepine) library] Koide, K.; Finkelstein, J. M.; Ball, Z.; Verdine, G. L. J. Am. Chem. Soc. 2001, 123, 398-408. (e) [1,3-Dioxane library] Sternson, S. M.; Louca, J. B.; Wong, J. C.; Schreiber, S. L. J. Am. Chem. Soc. 2001, 123, 1740-1747. (f) [Galanthamine library] Pelish, H. E.; Westwood, N. J.; Feng, Y.; Kirchhausen, T.; Shair, M. D. J. Am. Chem. Soc. 2001, 123, 6740-6741. (g) [Dihydropyrancarboxamide library] Stavenger, R. A.; Schreiber, S. L. Angew. Chem., Int. Ed. 2001, 40, 3417-3421. (h) [Hydroxamic acid library] Sternson, S. M.; Wong, J. C.; Grozinger, C. M.; Schreiber, S. L. Org. Lett. 2001, 3, 4239-4242. (i) [Biaryl library] Spring, D. R.; Krishnan, S.; Blackwell, H. E.; Schreiber, S. L. J. Am. Chem. Soc. 2002, 124, 1354-1363. (j) [Ferrier/Pauson-Khand library] Kubota, H.; Lim, J.; Depew, K. M.; Schreiber, S. L. Chem. Biol. 2002, 9, 265-276. (k) [Benzo[b]furan library] Liao, Y.; Reitman, M.; Zhang, Y.; Fathi, R.; Yang, Z. Org. Lett. 2002, 4, 2607-2609. (1) [Branched Diels-Alder skeletal diversity library] Kwon, O.; Park, S. B.; Schreiber, S. L. J. Am. Chem. Soc. 2002, 124, 13402-13404. (m) [Asymmetric azomethine ylide 1,3-dipolar cycloaddition library] Chen, C.; Li, X.; Schreiber, S. L. J. Am. Chem. Soc. 2003, 125, 10174-10175.
- (2001) J. Am. Chem. Soc. , vol.123 , pp. 1740-1747
- Sternson, S.M.¹ Louca, J.B.² Wong, J.C.³ Schreiber, S.L.⁴

10
- 0034809353
- Examples of diversity-oriented synthesis: (a) [Shikimic acid library] Tan, D. S.; Foley, M. A.; Stockwell, B. R.; Shair, M. D.; Schreiber, S. L. J. Am. Chem. Soc. 1999, 121, 9073-9087. (b) [Carpanone-like library] Lindsley, C. W.; Chan, L. K.; Goess, B. C.; Joseph, R.; Shair, M. D. J. Am. Chem. Soc. 2000, 122, 422-423. (c) [Ugi/Diels-Alder/RCM library] Lee, D.; Sello, J. K.; Schreiber, S. L. Org. Lett. 2000, 2, 709-712. (d) [THOX (tetrahydrooxazepine) library] Koide, K.; Finkelstein, J. M.; Ball, Z.; Verdine, G. L. J. Am. Chem. Soc. 2001, 123, 398-408. (e) [1,3-Dioxane library] Sternson, S. M.; Louca, J. B.; Wong, J. C.; Schreiber, S. L. J. Am. Chem. Soc. 2001, 123, 1740-1747. (f) [Galanthamine library] Pelish, H. E.; Westwood, N. J.; Feng, Y.; Kirchhausen, T.; Shair, M. D. J. Am. Chem. Soc. 2001, 123, 6740-6741. (g) [Dihydropyrancarboxamide library] Stavenger, R. A.; Schreiber, S. L. Angew. Chem., Int. Ed. 2001, 40, 3417-3421. (h) [Hydroxamic acid library] Sternson, S. M.; Wong, J. C.; Grozinger, C. M.; Schreiber, S. L. Org. Lett. 2001, 3, 4239-4242. (i) [Biaryl library] Spring, D. R.; Krishnan, S.; Blackwell, H. E.; Schreiber, S. L. J. Am. Chem. Soc. 2002, 124, 1354-1363. (j) [Ferrier/Pauson-Khand library] Kubota, H.; Lim, J.; Depew, K. M.; Schreiber, S. L. Chem. Biol. 2002, 9, 265-276. (k) [Benzo[b]furan library] Liao, Y.; Reitman, M.; Zhang, Y.; Fathi, R.; Yang, Z. Org. Lett. 2002, 4, 2607-2609. (1) [Branched Diels-Alder skeletal diversity library] Kwon, O.; Park, S. B.; Schreiber, S. L. J. Am. Chem. Soc. 2002, 124, 13402-13404. (m) [Asymmetric azomethine ylide 1,3-dipolar cycloaddition library] Chen, C.; Li, X.; Schreiber, S. L. J. Am. Chem. Soc. 2003, 125, 10174-10175.
- (2001) J. Am. Chem. Soc. , vol.123 , pp. 6740-6741
- Pelish, H.E.¹ Westwood, N.J.² Feng, Y.³ Kirchhausen, T.⁴ Shair, M.D.⁵

11
- 0035903515
- Examples of diversity-oriented synthesis: (a) [Shikimic acid library] Tan, D. S.; Foley, M. A.; Stockwell, B. R.; Shair, M. D.; Schreiber, S. L. J. Am. Chem. Soc. 1999, 121, 9073-9087. (b) [Carpanone-like library] Lindsley, C. W.; Chan, L. K.; Goess, B. C.; Joseph, R.; Shair, M. D. J. Am. Chem. Soc. 2000, 122, 422-423. (c) [Ugi/Diels-Alder/RCM library] Lee, D.; Sello, J. K.; Schreiber, S. L. Org. Lett. 2000, 2, 709-712. (d) [THOX (tetrahydrooxazepine) library] Koide, K.; Finkelstein, J. M.; Ball, Z.; Verdine, G. L. J. Am. Chem. Soc. 2001, 123, 398-408. (e) [1,3-Dioxane library] Sternson, S. M.; Louca, J. B.; Wong, J. C.; Schreiber, S. L. J. Am. Chem. Soc. 2001, 123, 1740-1747. (f) [Galanthamine library] Pelish, H. E.; Westwood, N. J.; Feng, Y.; Kirchhausen, T.; Shair, M. D. J. Am. Chem. Soc. 2001, 123, 6740-6741. (g) [Dihydropyrancarboxamide library] Stavenger, R. A.; Schreiber, S. L. Angew. Chem., Int. Ed. 2001, 40, 3417-3421. (h) [Hydroxamic acid library] Sternson, S. M.; Wong, J. C.; Grozinger, C. M.; Schreiber, S. L. Org. Lett. 2001, 3, 4239-4242. (i) [Biaryl library] Spring, D. R.; Krishnan, S.; Blackwell, H. E.; Schreiber, S. L. J. Am. Chem. Soc. 2002, 124, 1354-1363. (j) [Ferrier/Pauson-Khand library] Kubota, H.; Lim, J.; Depew, K. M.; Schreiber, S. L. Chem. Biol. 2002, 9, 265-276. (k) [Benzo[b]furan library] Liao, Y.; Reitman, M.; Zhang, Y.; Fathi, R.; Yang, Z. Org. Lett. 2002, 4, 2607-2609. (1) [Branched Diels-Alder skeletal diversity library] Kwon, O.; Park, S. B.; Schreiber, S. L. J. Am. Chem. Soc. 2002, 124, 13402-13404. (m) [Asymmetric azomethine ylide 1,3-dipolar cycloaddition library] Chen, C.; Li, X.; Schreiber, S. L. J. Am. Chem. Soc. 2003, 125, 10174-10175.
- (2001) Angew. Chem., Int. Ed. , vol.40 , pp. 3417-3421
- Stavenger, R.A.¹ Schreiber, S.L.²

12
- 0035961036
- Examples of diversity-oriented synthesis: (a) [Shikimic acid library] Tan, D. S.; Foley, M. A.; Stockwell, B. R.; Shair, M. D.; Schreiber, S. L. J. Am. Chem. Soc. 1999, 121, 9073-9087. (b) [Carpanone-like library] Lindsley, C. W.; Chan, L. K.; Goess, B. C.; Joseph, R.; Shair, M. D. J. Am. Chem. Soc. 2000, 122, 422-423. (c) [Ugi/Diels-Alder/RCM library] Lee, D.; Sello, J. K.; Schreiber, S. L. Org. Lett. 2000, 2, 709-712. (d) [THOX (tetrahydrooxazepine) library] Koide, K.; Finkelstein, J. M.; Ball, Z.; Verdine, G. L. J. Am. Chem. Soc. 2001, 123, 398-408. (e) [1,3-Dioxane library] Sternson, S. M.; Louca, J. B.; Wong, J. C.; Schreiber, S. L. J. Am. Chem. Soc. 2001, 123, 1740-1747. (f) [Galanthamine library] Pelish, H. E.; Westwood, N. J.; Feng, Y.; Kirchhausen, T.; Shair, M. D. J. Am. Chem. Soc. 2001, 123, 6740-6741. (g) [Dihydropyrancarboxamide library] Stavenger, R. A.; Schreiber, S. L. Angew. Chem., Int. Ed. 2001, 40, 3417-3421. (h) [Hydroxamic acid library] Sternson, S. M.; Wong, J. C.; Grozinger, C. M.; Schreiber, S. L. Org. Lett. 2001, 3, 4239-4242. (i) [Biaryl library] Spring, D. R.; Krishnan, S.; Blackwell, H. E.; Schreiber, S. L. J. Am. Chem. Soc. 2002, 124, 1354-1363. (j) [Ferrier/Pauson-Khand library] Kubota, H.; Lim, J.; Depew, K. M.; Schreiber, S. L. Chem. Biol. 2002, 9, 265-276. (k) [Benzo[b]furan library] Liao, Y.; Reitman, M.; Zhang, Y.; Fathi, R.; Yang, Z. Org. Lett. 2002, 4, 2607-2609. (1) [Branched Diels-Alder skeletal diversity library] Kwon, O.; Park, S. B.; Schreiber, S. L. J. Am. Chem. Soc. 2002, 124, 13402-13404. (m) [Asymmetric azomethine ylide 1,3-dipolar cycloaddition library] Chen, C.; Li, X.; Schreiber, S. L. J. Am. Chem. Soc. 2003, 125, 10174-10175.
- (2001) Org. Lett. , vol.3 , pp. 4239-4242
- Sternson, S.M.¹ Wong, J.C.² Grozinger, C.M.³ Schreiber, S.L.⁴

13
- 0037138650
- Examples of diversity-oriented synthesis: (a) [Shikimic acid library] Tan, D. S.; Foley, M. A.; Stockwell, B. R.; Shair, M. D.; Schreiber, S. L. J. Am. Chem. Soc. 1999, 121, 9073-9087. (b) [Carpanone-like library] Lindsley, C. W.; Chan, L. K.; Goess, B. C.; Joseph, R.; Shair, M. D. J. Am. Chem. Soc. 2000, 122, 422-423. (c) [Ugi/Diels-Alder/RCM library] Lee, D.; Sello, J. K.; Schreiber, S. L. Org. Lett. 2000, 2, 709-712. (d) [THOX (tetrahydrooxazepine) library] Koide, K.; Finkelstein, J. M.; Ball, Z.; Verdine, G. L. J. Am. Chem. Soc. 2001, 123, 398-408. (e) [1,3-Dioxane library] Sternson, S. M.; Louca, J. B.; Wong, J. C.; Schreiber, S. L. J. Am. Chem. Soc. 2001, 123, 1740-1747. (f) [Galanthamine library] Pelish, H. E.; Westwood, N. J.; Feng, Y.; Kirchhausen, T.; Shair, M. D. J. Am. Chem. Soc. 2001, 123, 6740-6741. (g) [Dihydropyrancarboxamide library] Stavenger, R. A.; Schreiber, S. L. Angew. Chem., Int. Ed. 2001, 40, 3417-3421. (h) [Hydroxamic acid library] Sternson, S. M.; Wong, J. C.; Grozinger, C. M.; Schreiber, S. L. Org. Lett. 2001, 3, 4239-4242. (i) [Biaryl library] Spring, D. R.; Krishnan, S.; Blackwell, H. E.; Schreiber, S. L. J. Am. Chem. Soc. 2002, 124, 1354-1363. (j) [Ferrier/Pauson-Khand library] Kubota, H.; Lim, J.; Depew, K. M.; Schreiber, S. L. Chem. Biol. 2002, 9, 265-276. (k) [Benzo[b]furan library] Liao, Y.; Reitman, M.; Zhang, Y.; Fathi, R.; Yang, Z. Org. Lett. 2002, 4, 2607-2609. (1) [Branched Diels-Alder skeletal diversity library] Kwon, O.; Park, S. B.; Schreiber, S. L. J. Am. Chem. Soc. 2002, 124, 13402-13404. (m) [Asymmetric azomethine ylide 1,3-dipolar cycloaddition library] Chen, C.; Li, X.; Schreiber, S. L. J. Am. Chem. Soc. 2003, 125, 10174-10175.
- (2002) J. Am. Chem. Soc. , vol.124 , pp. 1354-1363
- Spring, D.R.¹ Krishnan, S.² Blackwell, H.E.³ Schreiber, S.L.⁴

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