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Volumn , Issue 4, 2008, Pages 547-550

Tandem retro-Michael addition-Claisen rearrangement-intramolecular cyclization: One-pot synthesis of densely functionalized ethyl dihydropyrimidine-4-carboxylates from simple building blocks

(1) Naidu, B Narasimhulu a

a BRISTOL MYERS SQUIBB (United States)

Author keywords

1,6 dihydropyrimidine 4 carboxylates; Claisen rearrangement; Intramolecular cyclization; Retro Michael addition

Indexed keywords

CARBOXYLIC ACID DERIVATIVE; ESTER DERIVATIVE; PYRIMIDINONE DERIVATIVE; XYLENE;

ARTICLE; CLAISEN REARRANGEMENT; CYCLIZATION; MICHAEL ADDITION; ONE POT SYNTHESIS; PYROLYSIS; SUBSTITUTION REACTION;

EID: 41049110014 PISSN: 09365214 EISSN: None Source Type: Journal
DOI: 10.1055/s-2008-1032088 Document Type: Article

Times cited : (8)

References (12)

1
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- (1962) The Chemistry of Heterocyclic Compounds , vol.16
- Brown, J.D.¹

2
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- Wiley: Chichester
- (b) Hurst, D. T. An Introduction to the Chemistry and Biochemistry of Pyrimidines, Purines and Pteridines; Wiley: Chichester, 1980.
- (1980) An Introduction to the Chemistry and Biochemistry of Pyrimidines, Purines and Pteridines
- Hurst, D.T.¹

3
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- Sunderland, C. J.; Botta, M.; Aime, S.; Raymond, K. N. Inorg. Chem. 2001, 40, 6746.
- (2001) Inorg. Chem , vol.40 , pp. 6746
- Sunderland, C.J.¹ Botta, M.² Aime, S.³ Raymond, K.N.⁴

4
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- (a) Summa, V.; Petrocchi, A.; Matassa, V. G.; Taliani, M.; Laufer, R.; Francesco, R. D.; Altamura, S.; Pace, P. J. Med. Chem. 2004, 47, 5336.
- (2004) J. Med. Chem , vol.47 , pp. 5336
- Summa, V.¹ Petrocchi, A.² Matassa, V.G.³ Taliani, M.⁴ Laufer, R.⁵ Francesco, R.D.⁶ Altamura, S.⁷ Pace, P.⁸

5
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- (b) Stansfield, I.; Avolio, S.; Colarusso, S.; Gennari, N.; Narjes, F.; Picini, B.; Ponzi, S.; Harper, S. Bioorg. Med. Chem. Lett. 2004, 14, 5085.
- (2004) Bioorg. Med. Chem. Lett , vol.14 , pp. 5085
- Stansfield, I.¹ Avolio, S.² Colarusso, S.³ Gennari, N.⁴ Narjes, F.⁵ Picini, B.⁶ Ponzi, S.⁷ Harper, S.⁸

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- Culbertson, T. P. J. Heterocycl. Chem. 1979, 16, 1423.
- (1979) J. Heterocycl. Chem , vol.16 , pp. 1423
- Culbertson, T.P.¹

7
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- For related work, see: a
- For related work, see: (a) Colarusso, S.; Attenni, B.; Avolio, S.; Malancona, S.; Harper, S.; Altamura, S.; Koch, U.; Narjes, F. ARKIVOC 2006, (vii), 479.
- (2006) ARKIVOC , Issue.VII , pp. 479
- Colarusso, S.¹ Attenni, B.² Avolio, S.³ Malancona, S.⁴ Harper, S.⁵ Altamura, S.⁶ Koch, U.⁷ Narjes, F.⁸

8
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- (b) Kinzel, O. D.; Monteagudo, E.; Muraglia, E.; Orvieto, F.; Pescatore, G.; Rico Ferreira, M.; Rowley, M.; Summa, V. Tetrahedron Lett. 2007, 48, 6552.
- (2007) Tetrahedron Lett , vol.48 , pp. 6552
- Kinzel, O.D.¹ Monteagudo, E.² Muraglia, E.³ Orvieto, F.⁴ Pescatore, G.⁵ Rico Ferreira, M.⁶ Rowley, M.⁷ Summa, V.⁸

9
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- (c) Ferrara, M.; Crescenzi, B.; Donghi, M.; Muraglia, E.; Nizi, E.; Pesci, S.; Summa, V.; Gardelli, C. Tetrahedron Lett. 2007, 48, 8379.
- (2007) Tetrahedron Lett , vol.48 , pp. 8379
- Ferrara, M.¹ Crescenzi, B.² Donghi, M.³ Muraglia, E.⁴ Nizi, E.⁵ Pesci, S.⁶ Summa, V.⁷ Gardelli, C.⁸

10
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- Naidu, B.N.¹ Sorenson, M.E.²

11
- 41049084804
- Representative Procedures Method A: A solution of 6e (2.68 g, 7.52 mmol) in xylenes (50 mL) was heated at reflux for 1.5 h and cooled to r.t. The precipitate was filtered and dried to give 2e as an off-white solid (1.4 g, 60% yield, Method B: A solution of 6j (9.77 g, 29.22 mmol) in xylenes (100 mL) was heated at reflux for 5 h and cooled. Then, the reaction mixture was diluted with EtOAc (100 mL) and extracted with 0.5 M Na2CO3 (3 x 30 mL, The combined aqueous layers were acidified with coned HCl and extracted with CH2Cl2 (4 x 50 mL, The combined CH2Cl2 layers were dried (Na 2SO4, filtered, and concentrated to give a brown solid which was triturated with Et2O and filtered to afford 2j as a light-brown powder 4.32 g, 51
- 2O and filtered to afford 2j as a light-brown powder (4.32 g, 51%).

12
- 41049113246
- Analytical Data for New Compounds Compound 2a: 1H NMR (500 MHz, CDCl3, δ, 10.76 (1 H, s, 7.49-7.46 (5 H, m, 4.48 (2 H, q, J, 7.0 Hz, 3.45 (3 H, s, 1.41 (3 H, t, J, 7.0 Hz, HRMS: m/z calcd for C14H 15N2O4 [M, H, 275.1032; found: 275.1042. Anal. Calcd for C14H14N2O4: C, 61.30; H, 5.14; N, 10.21. Found: C, 61.31; H, 5.10; N, 10.21. Compound 2b: 1H NMR (500 MHz, CDCl3, δ, 10.63 (1 H, s, 7.39-7.23 (3 H, m, 4.49 (2 H, q, J, 7.0 Hz, 3.47 (3 H, s, 1.42 (3 H, t, J, 7.0 Hz, HRMS, m/z calcd for C14H 13F2N2O4 [M, H, 311.0844; found: 311.0832. Anal. Calcd for C14H14N2O 4: C, 54.19; H, 3.89; N, 9.03. Found: C, 54.21; H, 3.85; N, 8.85. Compound 2c: 1H NMR 500
- 4 [M + H]: 289.1188.

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