SCOPUS 정보 검색 플랫폼

Volumn , Issue 3, 2009, Pages 411-416

The Baylis-Hillman bromides as versatile synthons: A facile one-pot synthesis of indolizine and benzofused indolizine frameworks

(4) Basavaiah, Deevi a Devendar, Badugu a Lenin, Dandamudi V a Satyanarayana, Tummanapalli a

a UNIVERSITY OF HYDERABAD (India)

Author keywords

1,5 cyclization strategy; Baylis Hillman bromides; Benzofused indolizines; Indolizines; Isoquinoline; Quinoline

Indexed keywords

EID: 62249132328 PISSN: 09365214 EISSN: 14372096 Source Type: Journal
DOI: 10.1055/s-0028-1087533 Document Type: Article

Times cited : (80)

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- (b) Bode, M. L.; Kaye, P. T. J. Chem. Soc., Perkin Trans. 1 1990, 2612.
- (1990) J. Chem. Soc., Perkin Trans. 1 , pp. 2612
- Bode, M.L.¹ Kaye, P.T.²

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- 4 following the literature procedure. See: (a) Buchholz, R.; Hoffmann, H. M. R. Helv. Chim. Acta 1991, 74, 1213.
- 4 following the literature procedure. See: (a) Buchholz, R.; Hoffmann, H. M. R. Helv. Chim. Acta 1991, 74, 1213.

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- (b) Ameer, F.; Drewes, S. E.; Emslie, N. D.; Kaye, P. T.; Mann, R. L. J. Chem. Soc., Perkin Trans. 1 1983, 2293.
- (1983) J. Chem. Soc., Perkin Trans. 1 , pp. 2293
- Ameer, F.¹ Drewes, S.E.² Emslie, N.D.³ Kaye, P.T.⁴ Mann, R.L.⁵

83
- 62249179739
- 1-Aza-8-cyano-7-phenylbicyclo[4.3.0]nona-2,4,6,8-tetraene (2a, Representative Procedure To 2-(bromomethyl)-3-phenylprop-2-enenitrile 10 (1 mmol, 0.222 g) pyridine (3 mL) was added and stirred for 15 min (formation of pyridinium salt was observed as shown by TLC) at r.t. The reaction mixture was diluted with DMF (3 mL) and K2CO3 (5 mmol, 0.690 g) was added. The reaction mixture was then heated at 80°C for 3 h and was allowed to cool to r.t. Saturated aq NaCl soln (5 mL) was added and extracted with CH2Cl2 (5 x 10 mL, The combined organic layer was dried over anhyd Na2SO4. Solvent was evaporated, and the residue, thus obtained, was purified by column chromatography (SiO 2, 5% EtOAc in hexanes) to furnish the pure compound 2a as a colorless solid. Yield 52, 0.114 g, mp 128-130°C. 1H NMR (400 MHz, CDCl3, δ, 6.60-6.70 (m, 1 H, 6.77-6.86 m, 1 H
- 2: C, 82.55; H, 4.62; N, 12.84. Found: C, 82.51; H, 4.65; N, 12.70.

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- Detailed X-ray crystallographic data are available from the CCDC, 12 Union road, Cambridge CB2 1EZ, UK; for compounds 2a (CCDC # 693505), 3a (CCDC # 693506), 4a (CCDC # 693507).
- Detailed X-ray crystallographic data are available from the CCDC, 12 Union road, Cambridge CB2 1EZ, UK; for compounds 2a (CCDC # 693505), 3a (CCDC # 693506), 4a (CCDC # 693507).

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- 1-Aza-12-cyano-11-phenyltricyclo[8.3.0.02,7]trideca-2,4,-6, 8,10,12-hexaene (3a, Representative Procedure To a stirred solution of 2-(bromomethyl)-3-phenylprop-2-enenitrile (1 mmol, 0.222 g) in DMF (3 mL) was added quinoline (2 mmol, 0.258 g) at r.t. After stirring for 1 h (salt formation was observed as evidenced by TLC, K2CO3 (5 mmol, 0.690 g) was added and heated for 5 h at 80°C. The reaction mixture was allowed to cool to r.t. and diluted with sat. aq NaCl soln (5 mL) and extracted with CH2Cl2 (5 x 10 mL, The combined organic layers were dried over anhyd Na2SO4. Solvent was evaporated, and the residue, thus obtained, was purified by column chromatography (SiO2, 8% EtOAc in hexanes) to furnish the pure compound 3a as a colorless solid. Yield 45, 0.120 g, mp 160-162°C. 1H NMR (400 MHz, CDCl3, δ, 7.11 d, 1 H, J, 9.6 Hz, 7.34-7.68
- 2: C, 85.05; H, 4.51; N, 10.44. Found: C, 85.11; H, 4.54; N, 10.57.

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- The single crystal X-ray structure revealed the presence of two molecules in the asymmetric unit. For clarity we have shown one molecule in the ORTEP diagram
- The single crystal X-ray structure revealed the presence of two molecules in the asymmetric unit. For clarity we have shown one molecule in the ORTEP diagram.

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