SCOPUS 정보 검색 플랫폼

Volumn 21, Issue 1, 2010, Pages 35-38

Facile and efficient synthesis of quinoline-4-carboxylic acids under microwave irradiation

Author keywords

Microwave irradiation; Pfitzinger reaction; Quinoline 4 carboxylic acids

Indexed keywords

EID: 70749084300 PISSN: 10018417 EISSN: None Source Type: Journal
DOI: 10.1016/j.cclet.2009.09.012 Document Type: Article

Times cited : (32)

References (23)

1
- 0034570227
- Strigáćová J., and Hudecová D. Folia Microbiol. 45 (2000) 305
- (2000) Folia Microbiol. , vol.45 , pp. 305
- Strigáćová, J.¹ Hudecová, D.²

2
- 28244463489
- Holla B.S., Poojary K.N., et al. Indian J. Chem. Sect. B 44 (2005) 2114
- (2005) Indian J. Chem. Sect. B , vol.44 , pp. 2114
- Holla, B.S.¹ Poojary, K.N.²

3
- 0034066880
- Stemp G., Ashmeade T., et al. J. Med. Chem. 43 (2000) 1878
- (2000) J. Med. Chem. , vol.43 , pp. 1878
- Stemp, G.¹ Ashmeade, T.²

4
- 38949131438
- Smith P.W., and Dawson L.A. Drug Discov. 3 (2008) 1
- (2008) Drug Discov. , vol.3 , pp. 1
- Smith, P.W.¹ Dawson, L.A.²

5
- 33846217395
- Kaila N., Janz K., et al. J. Med. Chem. 50 (2007) 21
- (2007) J. Med. Chem. , vol.50 , pp. 21
- Kaila, N.¹ Janz, K.²

6
- 0001939679
- Pfitzinger W.J. J. Prakt. Chem. 33 (1886) 100
- (1886) J. Prakt. Chem. , vol.33 , pp. 100
- Pfitzinger, W.J.¹

7
- 70749147826
- Karen L., and Sternbach D.D. Synthesis (1993) 993
- (1993) Synthesis , pp. 993
- Karen, L.¹ Sternbach, D.D.²

8
- 0036422037
- Shvekhgeimer M.G., and Kondrashova N.N. Dokl. Akad. Nauk. 383 (2002) 221
- (2002) Dokl. Akad. Nauk. , vol.383 , pp. 221
- Shvekhgeimer, M.G.¹ Kondrashova, N.N.²

9
- 0007005152
- Doebner O. Bericht 16 (1883) 2357
- (1883) Bericht , vol.16 , pp. 2357
- Doebner, O.¹

10
- 0042592983
- Park S.H. Bull. Korean Chem. Soc. 24 (2003) 677
- (2003) Bull. Korean Chem. Soc. , vol.24 , pp. 677
- Park, S.H.¹

11
- 27744450163
- Duvelleroy D., Perrio C., et al. Org. Biomol. Chem. 3 (2005) 3794
- (2005) Org. Biomol. Chem. , vol.3 , pp. 3794
- Duvelleroy, D.¹ Perrio, C.²

12
- 0037148197
- Sakaguchi S., Shibamoto A., et al. Chem. Commun. (2002) 180
- (2002) Chem. Commun. , pp. 180
- Sakaguchi, S.¹ Shibamoto, A.²

13
- 0013632661
- Campbell K.N. J. Org. Chem. 11 (1946) 803
- (1946) J. Org. Chem. , vol.11 , pp. 803
- Campbell, K.N.¹

14
- 33947440007
- Phillips P. J. Am. Chem. Soc. 68 (1946) 2568
- (1946) J. Am. Chem. Soc. , vol.68 , pp. 2568
- Phillips, P.¹

15
- 0037416901
- Dumouchel S., Mongin F., et al. Tetrahedron Lett. 44 (2003) 2033
- (2003) Tetrahedron Lett. , vol.44 , pp. 2033
- Dumouchel, S.¹ Mongin, F.²

16
- 33947444910
- Renshaw R.R. J. Am. Chem. Soc. 61 (1939) 3320
- (1939) J. Am. Chem. Soc. , vol.61 , pp. 3320
- Renshaw, R.R.¹

17
- 33947444996
- Senear A.E., and Mead J.F. J. Am. Chem. Soc. 68 (1946) 2695
- (1946) J. Am. Chem. Soc. , vol.68 , pp. 2695
- Senear, A.E.¹ Mead, J.F.²

18
- 0346476214
- Brasyunas V.B., and Andreyanova A.T. Chem. Heterocycl. Compd. 24 (1988) 670
- (1988) Chem. Heterocycl. Compd. , vol.24 , pp. 670
- Brasyunas, V.B.¹ Andreyanova, A.T.²

19
- 24744432259
- Ashry H.E., and Ramadan E.S. Synth. Commun. 35 (2005) 2243
- (2005) Synth. Commun. , vol.35 , pp. 2243
- Ashry, H.E.¹ Ramadan, E.S.²

20
- 0035594725
- Silva J.F., Garden S.J., et al. J. Braz. Chem. Soc. 12 (2001) 273
- (2001) J. Braz. Chem. Soc. , vol.12 , pp. 273
- Silva, J.F.¹ Garden, S.J.²

21
- 3342879250
- Shvekhgeimer M.G. Chem. Heterocycl. Compd. 40 (2004) 257
- (2004) Chem. Heterocycl. Compd. , vol.40 , pp. 257
- Shvekhgeimer, M.G.¹

22
- 70749115095
- General procedure for the synthesis of 2a: A mixture of isatin 1a (1.0 mmol) and sodium pyruvate (1.2 mmol) were placed in a microwave test tube (10 mL) containing a magnetic stirring bar, rubber cap, and 4 mL of 20% aqueous NaOH. The test tube was subjected to MW at 110 °C (110 W) for 10-15 min. The internal pressure of the reaction vessel never surpassed 6 bar. After completion of the reaction, the tube was removed, cooled to room temperature, The reaction solution was acidified to pH 2 with 1 mol/L aqueous hydrochloric acid. The precipitate was collected by filtration, washed with water, and dried under vacuum. The crude product was purified by recrystallization from hot water. mp: 235-240 °C; 1H NMR (DMSO-d6, δ 8.81 (d, 1H, J, 7.6 Hz, 8.48 (s, 1H, 8.26 (d, 1H, J, 7.8 Hz, 7.95 (m, 1H, 7.86(m, 1H, 13C NMR (DMSO-d6, δ 167.4, 166.2, 148.9, 148.3, 137.6, 131.2, 131.0, 130.5, 126.0, 125.9, 122.0; HRMS (ESI) m/z cal
- 4 (M+H) 218.0375, found 218.0363.

23
- 70749130830
- General procedure for the synthesis of 3a: A suspension of QDCs 2a (1.0 mmol) were placed in a microwave test tube (10 mL) containing a magnetic stirring bar, rubber cap, and 4 mL of water. The test tube was subjected to MW at 190-200 °C for 5 min. The internal pressure of the reaction vessel rised to 16-18 bar. After completion of the reaction, the tube was removed, cooled to room temperature. The precipitate was collected by filtration, washed with water, and dried under vacuum. The crude product was purified by recrystallization from hot water. mp: 255-258 °C; 1HNMR (DMSO-d6, δ 9.06 (d, 1H, J, 4.5 Hz, 8.72 (d, 1H, J, 8.7 Hz, 8.14 (d, 1H, J, 8.4 Hz, 7.95 (d, 1H, J, 4.2 Hz, 7.85(t, 1H, J, 7.0 Hz, 7.74(t, 1H, J, 7.0 Hz, 13C NMR (DMSO-d6, δ 169.0, 151.2, 147.0, 136.1, 132.3, 130.6, 129.9, 125.1, 124.7, 121.0; HRMS (ESI) m/z calcd. for C10H7NO2 (M+H) 174.0477, found 174.0471
- 2 (M+H) 174.0477, found 174.0471.

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