SCOPUS 정보 검색 플랫폼

Synlett

Volumn , Issue 14, 2007, Pages 2205-2208

Gas-phase pyrolysis in organic synthesis: Rapid green synthesis of 4-quinolinones

(4) Al Awadi, Nouria A a Abdelhamid, Ismail Abdelshafy a Al Etaibi, Alya M b Elnagdi, Mohamed Hilmy a

a KUWAIT UNIVERSITY (Kuwait)

b MANUFACTURING ENGINEERING DEPARTMENT (Kuwait)

Author keywords

4 quinolinones; Meldrum's acid; Pyrolysis

Indexed keywords

4 QUINOLINONE; 5 BROMO 1H QUINOLIN 4 ONE; 6 METHYL 1H QUINOLIN 4 ONE; 7 BROMO 1H QUINOLIN 4 ONE; AMINE; PYRAZINOL[1,2 A]PYRIMIDIN 4 ONE; QUINOLONE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CYCLIZATION; DRUG SYNTHESIS; GAS; PYROLYSIS; SUBSTITUTION REACTION;

EID: 34548735922 PISSN: 09365214 EISSN: None Source Type: Journal
DOI: 10.1055/s-2007-985573 Document Type: Article

Times cited : (45)

References (28)

1
- 33746157760
- Hiari, Y. M.; Khanfar, M. A.; Qaisi, A. M.; Abu Shuheil, M. Y.; El-Abadelah, M. M.; Boese, R. Heterocycles 2006, 68, 1163.
- (2006) Heterocycles , vol.68 , pp. 1163
- Hiari, Y.M.¹ Khanfar, M.A.² Qaisi, A.M.³ Abu Shuheil, M.Y.⁴ El-Abadelah, M.M.⁵ Boese, R.⁶

2
- 34548707931
- Bacteria and Antibacterial Agents; Biochemical & Medicinal Chemistry
- Oxford University Press: USA
- Mann, J.; Crabbe, M. J. C. Bacteria and Antibacterial Agents; Biochemical & Medicinal Chemistry Series, Oxford University Press: USA, 1996, 64.
- (1996) Series , pp. 64
- Mann, J.¹ Crabbe, M.J.C.²

3
- 0012016281
- Heindel, N. D.; Brodof, T. A.; Kogelschatz, J. E. J. Heterocycl. Chem. 1966, 3, 222.
- (1966) J. Heterocycl. Chem , vol.3 , pp. 222
- Heindel, N.D.¹ Brodof, T.A.² Kogelschatz, J.E.³

4
- 0012017104
- Wiley and Sons: New York
- (a) Lauer, W. M.; Kaslow, C. E. Org. Synth., Coll. Vol. III; Wiley and Sons: New York, 1955, 580.
- (1955) Org. Synth., Coll , vol.3 , pp. 580
- Lauer, W.M.¹ Kaslow, C.E.²

5
- 0042675437
- Wiley and Sons: New York
- (b) Reynolds, G. A.; Hauser, C. R. Org. Synth., Coll. Vol. III; Wiley and Sons: New York, 1955, 593.
- (1955) Org. Synth., Coll , vol.3 , pp. 593
- Reynolds, G.A.¹ Hauser, C.R.²

6
- 34548803525
- Wiley and Sons: New York
- Price, C. C.; Roberts, R. M. Org. Synth., Coll. Vol. III; Wiley and Sons: New York, 1955, 272.
- (1955) Org. Synth., Coll , vol.3 , pp. 272
- Price, C.C.¹ Roberts, R.M.²

7
- 85082554940
- Chen, B.; Huang, X.; Wang, J. Synthesis 1987, 482.
- (1987) Synthesis , pp. 482
- Chen, B.¹ Huang, X.² Wang, J.³

8
- 0004061172
- 4th ed, Blackwell Publishers: London
- Joule, J. A.; Mills, K. Heterocyclic Chemistry, 4th ed.; Blackwell Publishers: London, 2000, 133.
- (2000) Heterocyclic Chemistry , pp. 133
- Joule, J.A.¹ Mills, K.²

9
- 25844505060
- Al-Awadi, H.; Ibrahim, M. R.; Dib, H. H.; Al-Awadi, N. A.; Ibrahim, A. I. Tetrahedron 2005, 61, 10507.
- (2005) Tetrahedron , vol.61 , pp. 10507
- Al-Awadi, H.¹ Ibrahim, M.R.² Dib, H.H.³ Al-Awadi, N.A.⁴ Ibrahim, A.I.⁵

10
- 22544462206
- Al-Awadi, N. A.; George, B. J.; Dib, H. H.; Ibrahim, M. R.; Ibrahim, Y. A.; El-Dusouqui, O. M. Tetrahedron 2005, 61, 8257.
- (2005) Tetrahedron , vol.61 , pp. 8257
- Al-Awadi, N.A.¹ George, B.J.² Dib, H.H.³ Ibrahim, M.R.⁴ Ibrahim, Y.A.⁵ El-Dusouqui, O.M.⁶

11
- 0035906025
- Al-Awadi, N. A.; Elnagdi, M. H.; Ibrahim, Y. A.; Kaul, K.; Kumar, A. Tetrahedron 2001, 57, 1609.
- (2001) Tetrahedron , vol.57 , pp. 1609
- Al-Awadi, N.A.¹ Elnagdi, M.H.² Ibrahim, Y.A.³ Kaul, K.⁴ Kumar, A.⁵

12
- 37049082868
- Hickson, C. L.; Keith, E. M.; Martin, J. C.; McNab, H.; Monahan, L. C.; Walkinshaw, M. D. J. Chem. Soc., Perkin Trans. 1 1986, 1465.
- (1986) Chem. Soc., Perkin Trans. 1 , pp. 1465
- Hickson, C.L.¹ Keith, E.M.² Martin, J.C.³ McNab, H.⁴ Monahan, L.C.⁵ Walkinshaw, M.D.J.⁶

13
- 34548758481
- 13C NMR, IR and GC-MS. Relative and percent yields were determined from NMR.
- 13C NMR, IR and GC-MS. Relative and percent yields were determined from NMR.

14
- 34548738996
- Flash Vacuum Pyrolysis of 8a-j The sample was volatilized from a tube in a Buchi Kugelrohr oven through a 30 x 2.5 cm horizontal-fused quartz tube and was heated externally by a cabolite Eurotherm tube furnace MTF-12/38A to 600°C. The products were collected in a U-shaped trap cooled in liquid nitrogen. The whole system was maintained at a pressure of 10-2 Torr by an Edwards Model E2M5 high-capacity rotary oil pump, the pressure being measured by a Pirani gauge situated between the cold trap and pump. Under these condition the contact time in the hot zone was estimated to be 10 ms. Products collected in the U-shaped trap were analyzed by 1H NMR, 13C NMR, IR and GC-MS. Relative and percent yields were determined from NMR. Compounds 11a,c,d,f-h,j-n, 16, and 17 has been reported earlier and proved to be identical with products obtained here.19-27
- 19-27

15
- 34548727989
- 13C NMR (DMSO, 100 MHz): δ = 21.55, 109.09, 119.18, 124.70, 125.96, 134.31, 134.57, 138.67, 140.50, 178.48. DEPT 135: δ = 21.55, 109.09, 119.18, 124.70, 125.96, 134.57, 140.50.
- 13C NMR (DMSO, 100 MHz): δ = 21.55, 109.09, 119.18, 124.70, 125.96, 134.31, 134.57, 138.67, 140.50, 178.48. DEPT 135: δ = 21.55, 109.09, 119.18, 124.70, 125.96, 134.57, 140.50.

16
- 34548750942
- 13C NMR (100 MHz, DMSO): δ = 111.5, 120.4, 123.2, 126, 128.4, 132.7, 141, 143.4, 177.4.
- 13C NMR (100 MHz, DMSO): δ = 111.5, 120.4, 123.2, 126, 128.4, 132.7, 141, 143.4, 177.4.

17
- 34548751763
- 13C NMR (75 MHz, DMSO): δ = 110.3, 119.5, 121.5, 125.6, 127.2, 130.6, 139.3, 142, 177.
- 13C NMR (75 MHz, DMSO): δ = 110.3, 119.5, 121.5, 125.6, 127.2, 130.6, 139.3, 142, 177.

18
- 0003412412
- 5th ed, J. Wiley and Sons, Inc, New York
- Smith, M. B.; March, J. March's Advanced Organic Chemistry: Reaction Mechanisms and Structure, 5th ed.; J. Wiley and Sons, Inc.: New York, 2001, 68.
- (2001) March's Advanced Organic Chemistry: Reaction Mechanisms and Structure , pp. 68
- Smith, M.B.¹ March, J.²

19
- 34548709651
- 3O (147.14): C, 57.14; H, 3.43; N, 28.56. Found: C, 57.53; H, 3.62; N, 28.83.
- 3O (147.14): C, 57.14; H, 3.43; N, 28.56. Found: C, 57.53; H, 3.62; N, 28.83.

20
- 0037144639
- Huang, X.; Liu, Z. J. Org. Chem. 2002, 67, 6731.
- (2002) J. Org. Chem , vol.67 , pp. 6731
- Huang, X.¹ Liu, Z.²

21
- 11844271994
- Tois, J.; Vahermo, M.; Koskinen, A. Tetrahedron Lett. 2005, 46, 735.
- (2005) Tetrahedron Lett , vol.46 , pp. 735
- Tois, J.¹ Vahermo, M.² Koskinen, A.³

22
- 0035935156
- Huang, X.; Liu, Z. Tetrahedron Lett. 2001, 42, 7655.
- (2001) Tetrahedron Lett , vol.42 , pp. 7655
- Huang, X.¹ Liu, Z.²

23
- 0030878984
- Griera, R.; Armengol, M.; Reyes, A.; Alvarez, M.; Palomer, A.; Cabre, F.; Pascual, J.; Garcia, M. L.; Mauleon, D. Eur. J. Med. Chem. 1997, 547.
- (1997) Eur. J. Med. Chem , pp. 547
- Griera, R.¹ Armengol, M.² Reyes, A.³ Alvarez, M.⁴ Palomer, A.⁵ Cabre, F.⁶ Pascual, J.⁷ Garcia, M.L.⁸ Mauleon, D.⁹

24
- 33748421870
- Hirano, J.; Hamase, K.; Zaitsu, K. Tetrahedron 2006, 62, 10065.
- (2006) Tetrahedron , vol.62 , pp. 10065
- Hirano, J.¹ Hamase, K.² Zaitsu, K.³

25
- 84943961938
- For 5-OMe: Cassis, R.; Tapia, R.; Valderrama, J. Synth. Commun. 1995, 15, 125.
- For 5-OMe: Cassis, R.; Tapia, R.; Valderrama, J. Synth. Commun. 1995, 15, 125.

26
- 2942513563
- Ruchelman, A. L.; Kerrigan, J. E.; Li, T.-K.; Zhou, N.; Liu, A.; Liu, L. F.; LaVoie, E. J. Bioorg. Med. Chem. 2004, 12, 3731.
- (2004) Bioorg. Med. Chem , vol.12 , pp. 3731
- Ruchelman, A.L.¹ Kerrigan, J.E.² Li, T.-K.³ Zhou, N.⁴ Liu, A.⁵ Liu, L.F.⁶ LaVoie, E.J.⁷

27
- 33746582493
- Reimlinger, H.; Peiren, M. A.; Merenyi, R. Chem. Ber. 1972, 105, 794.
- (1972) Chem. Ber , vol.105 , pp. 794
- Reimlinger, H.¹ Peiren, M.A.² Merenyi, R.³

28
- 34548798069
- Czuba, W. C.; Kowalski, P.; Grzegozek, M. Pol. J. Chem. 1980, 54, 1573.
- (1980) Pol. J. Chem , vol.54 , pp. 1573
- Czuba, W.C.¹ Kowalski, P.² Grzegozek, M.³

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.