SCOPUS 정보 검색 플랫폼

Volumn , Issue 12, 2009, Pages 1929-1932

Efficient synthesis of functionalized 2,5-dihydropyrrole derivatives by Ph3P-promoted condensation between acetylene esters and α-arylamino ketones

(3) Anary Abbasinejad, Mohammad a Poorhassan, Ehsanorreza a Hassanabadi, Alireza a

a ISLAMIC AZAD UNIVERSITY (Iran)

Author keywords

aminoketones; 2,5 dihydropyrroles; Dialkyl acetylenedicarboxylates; Intramolecular Wittig reaction; Triphenylphosphine

Indexed keywords

ACETYLENE DERIVATIVE; ALKYL GROUP; AROMATIC AMINE; CARBOXYLIC ACID DERIVATIVE; CHROMIUM DERIVATIVE; ESTER DERIVATIVE; KETONE DERIVATIVE; PYRROLE DERIVATIVE; TRIPHENYLPHOSPHINE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; INFRARED SPECTROSCOPY; ONE POT SYNTHESIS; OXIDATION; POLYMERIZATION; PROTON NUCLEAR MAGNETIC RESONANCE; QUANTUM YIELD; REACTION ANALYSIS;

EID: 67749145447 PISSN: 09365214 EISSN: 14372096 Source Type: Journal
DOI: 10.1055/s-0029-1217516 Document Type: Article

Times cited : (18)

References (23)

1
- 0003942757
- Wiley: New York
- Laszlo, P. Organic Reactions: Simplicity and Logic; Wiley: New York, 1995.
- (1995) Organic Reactions: Simplicity and Logic
- Laszlo, P.¹

2
- 33144455399
- Garbaccio, R. M.; Fraley, M. E.; Tasber, E. S.; Olson, C. M.; Hoffman, w. F.; Arrington, K. L.; Torrent, M.; Buser, C. A.; Walsh, E. S.; Hamilton, K.; Schaber, M. D.; Fernandes, C.; Lobell, R. B.; Tao, W.; South, V. J.; Yan, Y.; Kuo, L. C.; Prueksaritanont, T.; Slaughter, D. E.; Shu, C.; Heimbrook, D. C.; Kohl, N. E.; Huber, H. E.; Hartman, G. D. Bioorg. Med. Chem. Lett. 2006, 16, 1780.
- (2006) Bioorg. Med. Chem. Lett , vol.16 , pp. 1780
- Garbaccio, R.M.¹ Fraley, M.E.² Tasber, E.S.³ Olson, C.M.⁴ Hoffman, W.F.⁵ Arrington, K.L.⁶ Torrent, M.⁷ Buser, C.A.⁸ Walsh, E.S.⁹ Hamilton, K.¹⁰ Schaber, M.D.¹¹ Fernandes, C.¹² Lobell, R.B.¹³ Tao, W.¹⁴ South, V.J.¹⁵ Yan, Y.¹⁶ Kuo, L.C.¹⁷ Prueksaritanont, T.¹⁸ Slaughter, D.E.¹⁹ Shu, C.²⁰ more..

3
- 20844434822
- Chen, Y.; Zeng, D. Z.; Xie, N.; Dang, Y. Z. J. Org. Chem. 2005, 70, 5001.
- (2005) J. Org. Chem , vol.70 , pp. 5001
- Chen, Y.¹ Zeng, D.Z.² Xie, N.³ Dang, Y.Z.⁴

4
- 67749145021
- U.S. Patent 4,909,828
- Hinio, T. K.; Machida, T. G.; Hino, A. K.; Oume, A. Y.; Hachioji, H. M. U.S. Patent 4,909,828, 1990.
- (1990)
- Hinio, T.K.¹ Machida, T.G.² Hino, A.K.³ Oume, A.Y.⁴ Hachioji, H.M.⁵

5
- 67749136736
- U.S. Patent 4,220,655
- Bohner, B.; Baumann, M. U.S. Patent 4,220,655, 1980.
- (1980)
- Bohner, B.¹ Baumann, M.²

6
- 67749134864
- Tarnavsky, S. S.; Dubinina, G. G.; Golovach, S. M.; Yarmoluk, S. M. Biopolym. Cell 2003, 19, 548.
- (2003) Biopolym. Cell , vol.19 , pp. 548
- Tarnavsky, S.S.¹ Dubinina, G.G.² Golovach, S.M.³ Yarmoluk, S.M.⁴

7
- 13644249111
- Banks, C. E.; Evans, R. G.; Rodrigues, J.; Turner, P. G.; Donohoe, T. J.; Compton, R. G. Tetrahedron 2005, 61, 2365.
- (2005) Tetrahedron , vol.61 , pp. 2365
- Banks, C.E.¹ Evans, R.G.² Rodrigues, J.³ Turner, P.G.⁴ Donohoe, T.J.⁵ Compton, R.G.⁶

8
- 1542358701
- Kim, J. M.; Lee, K. Y.; Lee, S.; Kim, J. N. Tetrahedron Lett. 2004, 45, 2805.
- (2004) Tetrahedron Lett , vol.45 , pp. 2805
- Kim, J.M.¹ Lee, K.Y.² Lee, S.³ Kim, J.N.⁴

9
- 0345731484
- Ruano, J. L. G.; Tito, A.; Peromingo, M. T. J. Org. Chem. 2003, 68, 10013.
- (2003) J. Org. Chem , vol.68 , pp. 10013
- Ruano, J.L.G.¹ Tito, A.² Peromingo, M.T.³

10
- 26244457214
- Yavari, I.; Moradi, L.; Nasiri, F.; Djahaniani, H. Monatsh. Chem. 2005, 136, 1757.
- (2005) Monatsh. Chem , vol.136 , pp. 1757
- Yavari, I.¹ Moradi, L.² Nasiri, F.³ Djahaniani, H.⁴

11
- 33644814420
- Yavari, I.; Ahmadian-Razlighi, L. Phosphorus, Sulfur Silicon 2006, 181, 771.
- (2006) Phosphorus, Sulfur Silicon , vol.181 , pp. 771
- Yavari, I.¹ Ahmadian-Razlighi, L.²

12
- 0037033205
- Evans, L. A.; Griffiths, K. E.; Guthmann, H.; Murphy, P. J. Tetrahedron Lett. 2002, 43, 299.
- (2002) Tetrahedron Lett , vol.43 , pp. 299
- Evans, L.A.¹ Griffiths, K.E.² Guthmann, H.³ Murphy, P.J.⁴

13
- 45849086863
- Anary-Abbasinejad, M.; Anaraki-Ardakani, H.; Hosseini-Mehdiabad, H. Phosphorus, Sulfur Silicon Relat. Elem. 2008, 183, 1440.
- (2008) Phosphorus, Sulfur Silicon Relat. Elem , vol.183 , pp. 1440
- Anary-Abbasinejad, M.¹ Anaraki-Ardakani, H.² Hosseini-Mehdiabad, H.³

14
- 54049149364
- Anary-Abbasinejad, M.; Mosslemin, M. H.; Hassanabadi, A.; Tabatabaee, M. Synth. Commun. 2008, 38, 3700.
- (2008) Synth. Commun , vol.38 , pp. 3700
- Anary-Abbasinejad, M.¹ Mosslemin, M.H.² Hassanabadi, A.³ Tabatabaee, M.⁴

15
- 35348994263
- Anary-Abbasinejad, M.; Hassanabadi, A.; Anaraki-Ardakani, H. J. Chem. Res. 2007, 455.
- (2007) J. Chem. Res , pp. 455
- Anary-Abbasinejad, M.¹ Hassanabadi, A.² Anaraki-Ardakani, H.³

16
- 67749094336
- General procedure for the preparation of compounds 3a-h: To a magnetically stirred solution of β-aminoketone (1 mmol) and triphenylphosphine (0.28 g, 1 mmol) in CH2Cl2 (10 mL, was added dropwise a mixture of dialkyl acetylenedicarboxylate (1 mmol) in CH 2Cl2 (5 mL) at room temperature. The reaction mixture was stirred for 24 h, then the solvent was removed under reduced pressure and the residue was purified by silica gel column chromatography (hexane-EtOAc, The solvent was removed under reduced pressure to afford the product. 3a: White powder; mp 110-112 ° C; IR (KBr, 1740, 1699 (ester) cm-1; Anal. Calcd for C21H20BrNO5: C, 56.52; H, 4.52; N, 3.14. Found: C, 56.51; H, 4.33; N, 3.17; MS: m/z, 445 (4, 1H NMR (500 MHz, CDCl3, δ, 3.70, 3.73 and 3.75 (9 H, 3 x s, 3 x OCH3, 4.50 1 H, dd, J, 15.7 Hz, J, 2.3 Hz
- 2)

17
- 0003449456
- 5th ed, Elsevier: Amsterdam
- Corbridge, D. E. C. Phosphorus: An Outline of its Chemistry, Biochemistry, and Uses, 5th ed.; Elsevier: Amsterdam, 1995.
- (1995) Phosphorus: An Outline of its Chemistry, Biochemistry, and Uses
- Corbridge, D.E.C.¹

18
- 85055947393
- CRC Press: Boca Raton FL
- Engel, R. Synthesis of Carbon-Phosphorus Bonds; CRC Press: Boca Raton FL, 1988.
- (1988) Synthesis of Carbon-Phosphorus Bonds
- Engel, R.¹

19
- 0001154962
- Kolodiazhnyi, O. I. Russ. Chem. Rev. 1997, 66, 225.
- (1997) Russ. Chem. Rev , vol.66 , pp. 225
- Kolodiazhnyi, O.I.¹

20
- 0001956611
- Bestmann, H. J.; Zimmermann, R. Top. Curr. Chem. 1983, 109, 85.
- (1983) Top. Curr. Chem , vol.109 , pp. 85
- Bestmann, H.J.¹ Zimmermann, R.²

21
- 0001848341
- Maryano, B. E.; Reits, A. B. Chem. Rev. 1989, 89, 863.
- (1989) Chem. Rev , vol.89 , pp. 863
- Maryano, B.E.¹ Reits, A.B.²

22
- 12044254595
- Pietrusiewiz, K. M.; Zablocka, M. Chem. Rev. 1994, 94, 1375.
- (1994) Chem. Rev , vol.94 , pp. 1375
- Pietrusiewiz, K.M.¹ Zablocka, M.²

23
- 67749121591
- General procedure for the preparation of compounds 7a-c: To a magnetically stirred solution of dihydropyrrole derivative 3 (1 mmol) in CHCl3 (10 mL, was added CrO3 (1 mmol) at room temperature. The reaction mixture was stirred for 4 h, then the solvent was removed under reduced pressure and the residue was purified by silica gel column chromatography (hexane-EtOAc, The solvent was removed under reduced pressure to afford the product. 7a: White powder; mp 123-125 ° C; IR (KBr, 1740, 1707 (ester) cm-1; Anal. Calcd for C21H 19NO5: C, 69.03; H, 5.24; N, 3.83. Found: C, 69.31; H, 5.19; N, 3.89; MS: m/z, 365 (34, 1H NMR (500 MHz, CDCl3, δ, 3.76, 3.86, 3.88 (9 H, 3 x s, 3 x OCH3, 6.98 and 7.30 (4 H, 2 x d, J, 9.0 Hz, ArH, 7.10 (1 H, s, CH of pyrrole, 7.28-7.45 (5 H, C6H5, 13C NMR 125.8 MHz, CDCl3
- 3), 113.1, 121.9, 123.8, 125.7, 126.7, 127.8, 130.2, 131.0, 131.7, 132.8, 133.6, 159.2 (aromatic and olefinic carbons), 160.8, 167.2 (2 x CO ester).

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