SCOPUS 정보 검색 플랫폼

Volumn , Issue 14, 2009, Pages 2253-2256

Copper-mediated N-arylation of quinazolinediones

Author keywords

Arylation; Boronic; Copper; Cross coupling; Heterocycle

Indexed keywords

BORONIC ACID DERIVATIVE; COPPER; PALLADIUM; QUINAZOLINE DERIVATIVE;

ARTICLE; ARYLATION; CATALYST; CROSS COUPLING REACTION; CYCLIZATION; DRUG SYNTHESIS; ONE POT SYNTHESIS;

EID: 69249102659 PISSN: 09365214 EISSN: 14372096 Source Type: Journal
DOI: 10.1055/s-0029-1217724 Document Type: Article

Times cited : (15)

References (30)

1
- 69249144759
- DE 2459090, 114468
- (a) Noda, K.; Nakagawa, A.; Hachiya, T.; Ide, H. DE 2459090, 1975; Chem. Abstr. 1975, 83, 114468.
- (1975) Chem. Abstr , vol.83
- Noda, K.¹ Nakagawa, A.² Hachiya, T.³ Ide, H.⁴

2
- 69249127391
- WO 9319068, 164213
- (b) Wilhelm, R.; Chin, R.; Lipp, R.; Devens, B.; Alvarez, R. WO 9319068, 1993; Chem. Abstr. 1993, 120, 164213.
- (1993) Chem. Abstr , vol.120
- Wilhelm, R.¹ Chin, R.² Lipp, R.³ Devens, B.⁴ Alvarez, R.⁵

3
- 0034606467
- (c) Crespo, M. I.; Gracia, J.; Puig, C.; Vega, A.; Bou, J.; Beleta, J.; Domenech, T.; Ryder, H.; Segarra, V.; Palacios, J. M. Bioorg. Med. Chem. Lett. 2000, 10, 2661.
- (2000) Bioorg. Med. Chem. Lett , vol.10 , pp. 2661
- Crespo, M.I.¹ Gracia, J.² Puig, C.³ Vega, A.⁴ Bou, J.⁵ Beleta, J.⁶ Domenech, T.⁷ Ryder, H.⁸ Segarra, V.⁹ Palacios, J.M.¹⁰

4
- 4344693094
- Takahashi, M.; Nagaoka, H.; Inoue, K. J. Heterocycl. Chem. 2004, 41, 525.
- (2004) J. Heterocycl. Chem , vol.41 , pp. 525
- Takahashi, M.¹ Nagaoka, H.² Inoue, K.³

5
- 21144433226
- Tran, T.; Ellsworth, E.; Watson, B.; Sanchez, J.; Showalter, H.; Rubin, J.; Stier, M.; Yip, J.; Nguyen, D.; Bird, P.; Singh, R. J. Heterocycl. Chem. 2005, 42, 669.
- (2005) J. Heterocycl. Chem , vol.42 , pp. 669
- Tran, T.¹ Ellsworth, E.² Watson, B.³ Sanchez, J.⁴ Showalter, H.⁵ Rubin, J.⁶ Stier, M.⁷ Yip, J.⁸ Nguyen, D.⁹ Bird, P.¹⁰ Singh, R.¹¹

6
- 0034974185
- Baraka, M. Boll. Chim. Farm. 2001, 140, 90.
- (2001) Boll. Chim. Farm , vol.140 , pp. 90
- Baraka, M.¹

7
- 26044465790
- Bhat, K.; Hayik, S.; Sztandera, L.; Bock, C. QSAR Comb. Sci. 2005, 24, 831.
- (2005) QSAR Comb. Sci , vol.24 , pp. 831
- Bhat, K.¹ Hayik, S.² Sztandera, L.³ Bock, C.⁴

8
- 84971062653
- Goldberg, I. Ber. Dtsch. Chem. Ges. 1906, 39, 1691.
- (1906) Ber. Dtsch. Chem. Ges , vol.39 , pp. 1691
- Goldberg, I.¹

9
- 0000157513
- (a) Muci, A. R.; Buchwald, S. Top. Curr. Chem. 2002, 219, 131.
- (2002) Top. Curr. Chem , vol.219 , pp. 131
- Muci, A.R.¹ Buchwald, S.²

10
- 0001038733
- (b) Wolfe, J.; Wagaw, S.; Marcoux, J.; Buchwald, S. Acc. Chem. Res. 1998, 31, 805.
- (1998) Acc. Chem. Res , vol.31 , pp. 805
- Wolfe, J.¹ Wagaw, S.² Marcoux, J.³ Buchwald, S.⁴

11
- 0032541260
- (c) Hartwig, J. Angew. Chem. Int. Ed. 1998, 37, 2046.
- (1998) Angew. Chem. Int. Ed , vol.37 , pp. 2046
- Hartwig, J.¹

12
- 9644277114
- (a) Beletskaya, I.; Cheprakov, A. Coord. Chem. Rev. 2004, 248, 2337.
- (2004) Coord. Chem. Rev , vol.248 , pp. 2337
- Beletskaya, I.¹ Cheprakov, A.²

13
- 0345708168
- (b) Thomas, A.; Ley, S. Angew. Chem. Int. Ed. 2003, 42, 5400.
- (2003) Angew. Chem. Int. Ed , vol.42 , pp. 5400
- Thomas, A.¹ Ley, S.²

14
- 0033593282
- (a) Goodbrand, H.; Hu, N. J. Org. Chem. 1999, 64, 670.
- (1999) J. Org. Chem , vol.64 , pp. 670
- Goodbrand, H.¹ Hu, N.²

15
- 0142074708
- (b) Patil, N.; Kelkar, A.; Nabi, Z.; Chaudhari, R. Chem. Commun. 2003, 2460.
- (2003) Chem. Commun , pp. 2460
- Patil, N.¹ Kelkar, A.² Nabi, Z.³ Chaudhari, R.⁴

16
- 0037178121
- Klapars, A.; Antilla, J.; Huang, X.; Buchwald, S. J. Am. Chem. Soc. 2002, 124, 7421.
- (2002) J. Am. Chem. Soc , vol.124 , pp. 7421
- Klapars, A.¹ Antilla, J.² Huang, X.³ Buchwald, S.⁴

17
- 0033515805
- (a) Kiyomori, A.; Marcoux, A.; Buchwald, S. Tetrahedron Lett. 1999, 40, 2657.
- (1999) Tetrahedron Lett , vol.40 , pp. 2657
- Kiyomori, A.¹ Marcoux, A.² Buchwald, S.³

18
- 0037009958
- (b) Antilla, J.; Klapars, A.; Buchwald, S. J. Am. Chem. Soc. 2002, 124, 11684.
- (2002) J. Am. Chem. Soc , vol.124 , pp. 11684
- Antilla, J.¹ Klapars, A.² Buchwald, S.³

19
- 33750917072
- Willis, M.; Snell, R.; Fletcher, A.; Woodward, R. Org. Lett. 2006, 8, 5089.
- (2006) Org. Lett , vol.8 , pp. 5089
- Willis, M.¹ Snell, R.² Fletcher, A.³ Woodward, R.⁴

20
- 0032492942
- Chan, D.; Monaco, K.; Wang, R.-P.; Winters, M. Tetrahedron Lett. 1998, 39, 2933.
- (1998) Tetrahedron Lett , vol.39 , pp. 2933
- Chan, D.¹ Monaco, K.² Wang, R.-P.³ Winters, M.⁴

21
- 0034625934
- Lam, P.; Deudon, K.; Averill, K.; Li, R.; He, M.; DeShong, P.; Clark, C. J. Am. Chem. Soc. 2000, 122, 7600.
- (2000) J. Am. Chem. Soc , vol.122 , pp. 7600
- Lam, P.¹ Deudon, K.² Averill, K.³ Li, R.⁴ He, M.⁵ DeShong, P.⁶ Clark, C.⁷

22
- 0030577490
- Chan, D. Tetrahedron Lett. 1996, 37, 9013.
- (1996) Tetrahedron Lett , vol.37 , pp. 9013
- Chan, D.¹

23
- 7444270527
- Kim, J.-J.; Park, Y.-D.; Cho, S.-D.; Kim, H.-K.; Chung, H.; Lee, S.-G.; Falck, J.; Yoon, Y.-J. Tetrahedron Lett. 2004, 45, 8781.
- (2004) Tetrahedron Lett , vol.45 , pp. 8781
- Kim, J.-J.¹ Park, Y.-D.² Cho, S.-D.³ Kim, H.-K.⁴ Chung, H.⁵ Lee, S.-G.⁶ Falck, J.⁷ Yoon, Y.-J.⁸

24
- 84889494843
- Hall, D, Ed, John Wiley and Sons: New York
- Hall, D. In Boronic Acids: Preparation and Applications in Organic Synthesis and Medicine; Hall, D., Ed.; John Wiley and Sons: New York, 2005, 1.
- (2005) Boronic Acids: Preparation and Applications in Organic Synthesis and Medicine , pp. 1
- Hall, D.¹

25
- 33751575313
- Jacobsen, M.; Knudsen, M.; Gothelf, K. J. Org. Chem. 2006, 71, 9183.
- (2006) J. Org. Chem , vol.71 , pp. 9183
- Jacobsen, M.¹ Knudsen, M.² Gothelf, K.³

26
- 69249095258
- A regiochemically controlled synthesis of quinazolinedione 3 was carried out using the route outlined in Scheme 1 (disconnection a). The material so obtained was spectroscopically identical to that generated by direct arylation of 1, confirming that the regiochemistry of substitution was limited to the free nitrogen position and not either of the available carbonyl oxygens.
- A regiochemically controlled synthesis of quinazolinedione 3 was carried out using the route outlined in Scheme 1 (disconnection a). The material so obtained was spectroscopically identical to that generated by direct arylation of 1, confirming that the regiochemistry of substitution was limited to the free nitrogen position and not either of the available carbonyl oxygens.

27
- 0032492980
- Evans, D.; Katz, J.; West, T. Tetrahedron Lett. 1998, 39, 2937.
- (1998) Tetrahedron Lett , vol.39 , pp. 2937
- Evans, D.¹ Katz, J.² West, T.³

28
- 69249090026
- Typical Procedure 3-Methylquinazoline-2,4 (1H,3H, dione (200 mg, 1.14 mmol, 4-methoxyphenylboronic acid (345 mg, 2.27 mmol, Cu(OAc)2 (412 mg, 2.27 mmol, and Et3N (0.316 mL, 2.27 mmol) were suspended in CH2Cl2 (12 mL) along with 200 mg of activated 4 Å MS. The suspension was allowed to stir at r.t. for 20 h then partitioned between 1 M HCl (50 mL) and EtOAc (50 mL, The organic layer was isolated, dried (MgSO4, and concentrated in vacuo, and the residue was purified by flash chromatography (15% EtOAc-i-hexane) to furnish 1-(4-methoxyphenyl)-3-methylquinazoline-2,4-(1H,3H)-dione (4) as a colourless solid (230 mg, 72, 1H NMR (400 MHz, CDCl3, δ, 8.1-8.4 (m, 1 H, 7.4-7.6 (m, 1 H, 7.1-7.3 (m, 3 H, 7.0-7.2 (d, 2 H, 6.59 (d, 1 H, 3.89 (s, 3 H, 3.52 (s, 3 H, 13C NMR 100 MHz, CDCl3, δ, 162.2, 159.9, 151.2, 141.7, 134.5, 129
- +.

29
- 0035858723
- (a) Lam, P.; Vincent, G.; Clark, C.; Deudon, S.; Jadhav, P. Tetrahedron Lett. 2001, 42, 3415.
- (2001) Tetrahedron Lett , vol.42 , pp. 3415
- Lam, P.¹ Vincent, G.² Clark, C.³ Deudon, S.⁴ Jadhav, P.⁵

30
- 0000290980
- (b) Collman, J.; Zhong, M. Org. Lett. 2000, 2, 1233.
- (2000) Org. Lett , vol.2 , pp. 1233
- Collman, J.¹ Zhong, M.²

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.