DOI: 10.1016/s0040-4039(02)00280-0. Zirconium(IV) chloride catalyzed one-pot synthesis of 3,4-dihydropyrimidin-2(1H)-ones

Zirconium(IV) chloride catalyzed one-pot synthesis of 3,4-dihydropyrimidin-2(1H)-ones

10.1016/s0040-4039(02)00280-0

Crossref journal-article

Elsevier BV

Tetrahedron Letters (78)

Bibliography

Reddy, Ch. V., Mahesh, M., Raju, P. V. K., Babu, T. R., & Reddy, V. V. N. (2002). Zirconium(IV) chloride catalyzed one-pot synthesis of 3,4-dihydropyrimidin-2(1H)-ones. Tetrahedron Letters, 43(14), 2657â2659.

Authors 5

Ch.Venkateshwar Reddy (first)
M Mahesh (additional)
P.V.K Raju (additional)
T.Ramesh Babu (additional)
V.V.Narayana Reddy (additional)

References 17 Referenced 274

10.1021/jo00286a020 / J. Org. Chem. by Atwal (1989)
10.1016/S0040-4020(97)00022-7 / Tetrahedron by Kappe (1997)
10.1021/jo00067a014 / J. Org. Chem. by Snider (1993)
{'key': '10.1016/S0040-4039(02)00280-0_BIB6', 'first-page': '360', 'volume': '23', 'author': 'Biginelli', 'year': '1893', 'journal-title': 'Gazz. Chem. Ital.'} / Gazz. Chem. Ital. by Biginelli (1893)
10.1016/S0040-4020(01)87971-0 / Tetrahedron by Kappe (1993)
10.1016/S0040-4039(01)80748-6 / Tetrahedron Lett. by Barluenga (1989)
10.3987/R-1987-05-1185 / Heterocycles by O'Reilly (1987)
10.1055/s-2001-14587 / Synlett by Ramalinga (2001)
10.1021/jo9821170 / J. Org. Chem. by Lenarsic (1999)
Firouzabadi, H.; Iranpoor, N.; Karimi, B. Synlett 1999, 3, 319 and 321. (10.1055/s-1999-2605)
10.1246/cl.1999.1339 / Chem. Lett. by Chary (1999)
{'key': '10.1016/S0040-4039(02)00280-0_BIB14', 'first-page': '683', 'volume': '5', 'author': 'Chary', 'year': '2000', 'journal-title': 'Synlett'} / Synlett by Chary (2000)
{'key': '10.1016/S0040-4039(02)00280-0_BIB15', 'first-page': '805', 'volume': '6', 'author': 'Karimi', 'year': '2000', 'journal-title': 'Synlett'} / Synlett by Karimi (2000)
10.1021/jo9919052 / J. Org. Chem. by Ma (2000)
10.1055/s-2001-15229 / Synthesis by Yadav (2001)
10.1055/s-1998-1764 / Synlett by Kappe (1998)
General procedure for the ZrCl4 catalyzed synthesis of pyrimidinones 4: A mixture containing an appropriate β-ketoester (5 mmol), corresponding aldehyde (5 mmol), urea or thiourea and ZrCl4 (10 mol%) in ethanol (15 ml) was refluxed for 4 h. After completion of the reaction, as indicated by TLC, the solvent was removed under reduced pressure to yield a solid, which was washed thoroughly with water, filtered and recrystallized from ethanol to afford pure product.Spectroscopic data. 4d: Mp 198–200°C; 1H NMR (DMSO-d6): δ 1.18 (t, J=7.5 Hz, 3H, CH3), 2.28 (s, 3H, CH3), 4.0 (q, J=7.5 Hz, 2H, -OCH2), 5.18 (s, 1H), 6.7 (d, J=8.9 Hz, 2H, Ar), 7.09 (d, J=8.9 Hz, 2H, Ar), 7.25 (s, 1H), 8.95 and 9.0 (2s, 2H, brs. NH). EIMS: m/z (%)=276 (10) (M+), 248 (100), 231 (28), 204 (80), 168 (87), 136 (48). IR (KBr): ν=3520, 3230, 3150, 1705, 1690 cm−1. Anal. calcd for C14H16N2O4: C, 60.86; H, 5.83; N, 10.17. Found: C, 60.81; H, 5.78; N, 10.11.4g: Mp 229–232°C; 1H NMR (DMSO-d6): δ 1.20 (t, J=7.6 Hz, 3H, CH3), 2.25 (s, 3H, CH3), 2.87 (s, 6H, N(CH3)2), 4.0 (q, J=7.6 Hz, 2H, -OCH2), 5.18 (s, 1H, CH), 6.62 (d, J=9.1 Hz, 2H, Ar), 7.19 (d, J=9.1 Hz, 2H, Ar), 8.90 and 8.95 (2s, 2H, brs. NH). EIMS: m/z (%)=303 (75) (M+), 274 (100), 257 (15), 230 (78), 155 (20). IR (KBr): ν=3200, 3100, 1700, 1685 cm−1.4l: Mp 190–192°C; 1H NMR (DMSO-d6): δ 1.19 (t, J=7.3 Hz, 3H, CH3), 2.27 (s, 3H, CH3), 4.08 (q, J=7.3 Hz, 2H, -OCH2), 5.22 (s, 1H, CH), 7.23 (m, 5H, Ar), 9.25 and 9.9 (2s, 2H, 2brs. NH). EIMS: m/z (%)=276 (65) (M+), 237 (45), 204 (100), 172 (35), 142 (20). IR (KBr): ν=3259, 3195, 3100, 1710, 1690 cm−1.4m: Mp 193–194°C; 1H NMR (DMSO-d6): δ 1.18 (t, J=7.5 Hz, 3H, CH3), 2.25 (s, 3H, CH3), 4.0 (q, J=7.5 Hz, 2H, -OCH2), 5.10 (s, 1H, CH), 6.65 (d, J=9.1 Hz, 2H, Ar), 7.00 (d, J=9.1 Hz, 2H, Ar), 9.10 (br. s, 1H, OH), 9.15 and 9.8 (2br. s, 2H, NH). EIMS: m/z (%)=292 (25) (M+), 264 (28), 220 (20), 200 (15), 142 (25), 50 (100). IR (KBr): ν=3450, 3190, 3040, 1705, 1650 cm−1.6a: Mp 160–162°C; 1H NMR (DMSO-d6): δ 0.85 (t, J=7.5 Hz, 3H, CH3), 3.10 (d, J=11.5 Hz, 1H, CH), 3.88 (q, J=7.5 Hz, 2H, -OCH2), 4.86 (d, J=11.5 Hz, 1H), 5.70 (br. s, 1H, NH), 5.72 (br. s, 1H, NH) 6.30 (s, 1H, OH), 7.36 (s, 5H, Ar). EIMS: m/z (%)=332 (80) (M+), 285 (20), 269 (75), 241 (100), 237 (72), 142 (25). IR (KBr): ν=3450, 3210, 1700, 1690 cm−1.6b: Mp 186–188°C; 1H NMR (DMSO-d6): δ 0.92 (t, J=7.3 Hz, 3H, CH3), 2.92 (d, J=11 Hz, 1H), 3.86 (q, J=7.3 Hz, 2H, -OCH2), 4.74 (d, J=11 Hz, 1H, CH), 6.65 (s, 1H), 6.70 (d, J=8.25 Hz, 2H, Ar), 6.96 (d, NH), 7.16 (d, J=9.1 Hz, 2H, Ar), 9.10 (s, 1H, NH). EIMS: m/z (%)=348 (75) (M+), 288 (30), 272 (70), 244 (100), 224 (65). IR (KBr): ν=3410, 3250, 3195, 1710, 1695 cm−1.

Dates

Type	When
Created	22 years, 4 months ago (April 4, 2003, 10:57 p.m.)
Deposited	6 years, 4 months ago (May 1, 2019, 3:51 p.m.)
Indexed	5 days, 6 hours ago (Aug. 29, 2025, 5:47 a.m.)
Issued	23 years, 5 months ago (April 1, 2002)
Published	23 years, 5 months ago (April 1, 2002)
Published Print	23 years, 5 months ago (April 1, 2002)

Funders 0

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BibTeX

@article{Reddy_2002, title={Zirconium(IV) chloride catalyzed one-pot synthesis of 3,4-dihydropyrimidin-2(1H)-ones}, volume={43}, ISSN={0040-4039}, url={http://dx.doi.org/10.1016/s0040-4039(02)00280-0}, DOI={10.1016/s0040-4039(02)00280-0}, number={14}, journal={Tetrahedron Letters}, publisher={Elsevier BV}, author={Reddy, Ch.Venkateshwar and Mahesh, M and Raju, P.V.K and Babu, T.Ramesh and Reddy, V.V.Narayana}, year={2002}, month=apr, pages={2657–2659} }

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      "unstructured": "General procedure for the ZrCl4 catalyzed synthesis of pyrimidinones 4: A mixture containing an appropriate \u03b2-ketoester (5 mmol), corresponding aldehyde (5 mmol), urea or thiourea and ZrCl4 (10 mol%) in ethanol (15 ml) was refluxed for 4 h. After completion of the reaction, as indicated by TLC, the solvent was removed under reduced pressure to yield a solid, which was washed thoroughly with water, filtered and recrystallized from ethanol to afford pure product.Spectroscopic data. 4d: Mp 198\u2013200\u00b0C; 1H NMR (DMSO-d6): \u03b4 1.18 (t, J=7.5 Hz, 3H, CH3), 2.28 (s, 3H, CH3), 4.0 (q, J=7.5 Hz, 2H, -OCH2), 5.18 (s, 1H), 6.7 (d, J=8.9 Hz, 2H, Ar), 7.09 (d, J=8.9 Hz, 2H, Ar), 7.25 (s, 1H), 8.95 and 9.0 (2s, 2H, brs. NH). EIMS: m/z (%)=276 (10) (M+), 248 (100), 231 (28), 204 (80), 168 (87), 136 (48). IR (KBr): \u03bd=3520, 3230, 3150, 1705, 1690 cm\u22121. Anal. calcd for C14H16N2O4: C, 60.86; H, 5.83; N, 10.17. Found: C, 60.81; H, 5.78; N, 10.11.4g: Mp 229\u2013232\u00b0C; 1H NMR (DMSO-d6): \u03b4 1.20 (t, J=7.6 Hz, 3H, CH3), 2.25 (s, 3H, CH3), 2.87 (s, 6H, N(CH3)2), 4.0 (q, J=7.6 Hz, 2H, -OCH2), 5.18 (s, 1H, CH), 6.62 (d, J=9.1 Hz, 2H, Ar), 7.19 (d, J=9.1 Hz, 2H, Ar), 8.90 and 8.95 (2s, 2H, brs. NH). EIMS: m/z (%)=303 (75) (M+), 274 (100), 257 (15), 230 (78), 155 (20). IR (KBr): \u03bd=3200, 3100, 1700, 1685 cm\u22121.4l: Mp 190\u2013192\u00b0C; 1H NMR (DMSO-d6): \u03b4 1.19 (t, J=7.3 Hz, 3H, CH3), 2.27 (s, 3H, CH3), 4.08 (q, J=7.3 Hz, 2H, -OCH2), 5.22 (s, 1H, CH), 7.23 (m, 5H, Ar), 9.25 and 9.9 (2s, 2H, 2brs. NH). EIMS: m/z (%)=276 (65) (M+), 237 (45), 204 (100), 172 (35), 142 (20). IR (KBr): \u03bd=3259, 3195, 3100, 1710, 1690 cm\u22121.4m: Mp 193\u2013194\u00b0C; 1H NMR (DMSO-d6): \u03b4 1.18 (t, J=7.5 Hz, 3H, CH3), 2.25 (s, 3H, CH3), 4.0 (q, J=7.5 Hz, 2H, -OCH2), 5.10 (s, 1H, CH), 6.65 (d, J=9.1 Hz, 2H, Ar), 7.00 (d, J=9.1 Hz, 2H, Ar), 9.10 (br. s, 1H, OH), 9.15 and 9.8 (2br. s, 2H, NH). EIMS: m/z (%)=292 (25) (M+), 264 (28), 220 (20), 200 (15), 142 (25), 50 (100). IR (KBr): \u03bd=3450, 3190, 3040, 1705, 1650 cm\u22121.6a: Mp 160\u2013162\u00b0C; 1H NMR (DMSO-d6): \u03b4 0.85 (t, J=7.5 Hz, 3H, CH3), 3.10 (d, J=11.5 Hz, 1H, CH), 3.88 (q, J=7.5 Hz, 2H, -OCH2), 4.86 (d, J=11.5 Hz, 1H), 5.70 (br. s, 1H, NH), 5.72 (br. s, 1H, NH) 6.30 (s, 1H, OH), 7.36 (s, 5H, Ar). EIMS: m/z (%)=332 (80) (M+), 285 (20), 269 (75), 241 (100), 237 (72), 142 (25). IR (KBr): \u03bd=3450, 3210, 1700, 1690 cm\u22121.6b: Mp 186\u2013188\u00b0C; 1H NMR (DMSO-d6): \u03b4 0.92 (t, J=7.3 Hz, 3H, CH3), 2.92 (d, J=11 Hz, 1H), 3.86 (q, J=7.3 Hz, 2H, -OCH2), 4.74 (d, J=11 Hz, 1H, CH), 6.65 (s, 1H), 6.70 (d, J=8.25 Hz, 2H, Ar), 6.96 (d, NH), 7.16 (d, J=9.1 Hz, 2H, Ar), 9.10 (s, 1H, NH). EIMS: m/z (%)=348 (75) (M+), 288 (30), 272 (70), 244 (100), 224 (65). IR (KBr): \u03bd=3410, 3250, 3195, 1710, 1695 cm\u22121."
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