How to cite this paper
APA: Rajua, C., Kalaipriya, M., Uma, R., Sridhar, R & Ramakrishna, S. (2012). Pyridinium Trifluoro Acetate Mediated Synthesis of 3,4-Dihydropyrimidin-2(1H)-ones and Tetrazolo[1,5-a]pyrimidine-6-carboxylates. Current Chemistry Letters, 1(1), 27-34.
Chicago/Turabian: Rajua, C., Kalaipriya, M., Uma, R., Sridhar, R & Ramakrishna, S. 2012. "Pyridinium Trifluoro Acetate Mediated Synthesis of 3,4-Dihydropyrimidin-2(1H)-ones and Tetrazolo[1,5-a]pyrimidine-6-carboxylates." Current Chemistry Letters 1, no. 1 (2012): 27-34.
AMA: Rajua, C., Kalaipriya, M., Uma, R., Sridhar, R & Ramakrishna, S. Pyridinium Trifluoro Acetate Mediated Synthesis of 3,4-Dihydropyrimidin-2(1H)-ones and Tetrazolo[1,5-a]pyrimidine-6-carboxylates. Current Chemistry Letters. 2012;1(1):27-34.
References
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2. Kappe C. O. (1993) 100 years of the biginelli dihydropyrimidine synthesis. Tetrahedron, 49, 6937.
3. Gein V. L., Mishunin V. V., Tsyplyakova E. P., Vinokurova O. V., and M. I. Vakhrin (2009) Synthesis and antimicrobial activity of methyl-7-aryl(heteryl)-6-(2-thienoyl)-4,7-Dihydrotetrazolo[1,5-a]pyrimidine-5-carboxylates. Pharmaceutical Chemistry Journal. 43, 12.
4. Atwal K. S., Swanson B. N., Unger S. E., Floyd D. M., Moreland S., Hedberg A., and O’Reilly, B. C. (1991) Dihydropyrimidine calcium channel blockers. 3.3-Carbamoyl-4-aryl-1, 2, 3, 4-tetrahydro-6-methyl-5-pyrimidinecarboxylic acid esters as orally effective antihypertensive agents. J. Med. Chem. 34, 806-811.
5. Grover G. J., Dzwonczyk S., McMullen D. M., Normandin D.E., Parham C. S., Sleph P. G., and Moreland S. (1995) Pharmacologic Profile of the Dihydropyrimidine Calcium Channel Blockers SQ 32,547 and SQ 32, 946. J. Cardiovasc. Pharmacol. 26, 289.
6. Dallinger D., and Kappe O. (2007) Rapid preparation of the mitotic kinesin Eg5 inhibitor monastrol using controlled microwave-assisted synthesis. Nature protocols, 2, 317.
7. Snider B. B., and Shi Z. (1993) Biomimetic Synthesis of (±)-Crambines A, B, C1, and C2. Revision of the Structure of Crambines B and C1. J. Org. Chem., 58, 3828.
8. Overman L. E., Rabinowitz M. H., and Renhowe P. A. (1995) J. Am.Chem. Soc., 117, 2657.
9. Aly A. (2006) Synthesis and pharmacological activity of annelated pyrimidine derivatives. Phosphorus, Sulfur Silicon Relat. Elem., 181, 1285.
10. Ismail M. A. H., Aboul-Einein M. N. Y., Abouzid K. A. M., and Kandil S. B. A. (2002) Synthesis of Certain 5,6,7,8-tetrahydrobenzo[b]thienopyrimidines Fused with Various Heterocyclic Ring Systems as Potential Antihypertensive Agents. Alex. J. Pharm. Sci., 15, 143.
11. Drizin I., Holladay M. W., Yi L., Zhang H. Q., Gopalakrishnan S.,Gopalakrishnan M., Whiteaker K. L., Buckner S.A., Sullivan J. P., Carroll W. (2002) Bioorg. Med. Chem. Lett., 12, 1481.
12. Nagai S. I., Ueda T., Sugiura S., Nagatsu A., Murakami N., Sakakibara J., Fujita M., and Hotta Y. (1998). Synthesis and central nervous system stimulant activity of 5,8-methanoquinazolines fused with 1,2,4-triazole, tetrazoleand 1,2,4-triazine J. Heterocyclic Chem., 35, 325.
13. Ranu B. C., Hajra A., and Jana U. (2000) Indium (III) chloride-catalyzed one-pot synthesis of dihydropyrimidinones by a three-component coupling of 1,3-dicarbonyl compounds, aldehydes, and urea: an improved procedure for the biginelli reaction. J. Org. Chem., 65, 6270-6276.
14. Paraskar A. S., Dewker G. K., and Sudalai A. (2003) Cu (OTf)2: a reusable catalyst for high-yield synthesis of 3,4-dihydropyrimidin-2(1H)-ones. Tetrahedron Lett., 44, 3305-3308.
15. Raju C., Uma R., Kalaipriya M., Sridhar R., Ramakrishna S. (2011) Ammonium trifluoro acetate mediated synthesis of 3, 4-dihydropyrimidin-2(1H)-ones. ISRN Organic Chemistry, doi:10.5402/2011/273136.
16. Saha S., and Moorthy J. N. (2011) Enantioselective organocatalytic biginelli reaction: Dependence of the catalyst on sterics, hydrogen bonding, and reinforced chirality. J. Org. Chem., 76 (2), 396-402.
17. Shobha D., Adharvana Chari M., and Ahn K. H. (2009) An efficient biginelli one-pot synthesis of new benzoxazole-substituted dihydropyrimidinones and thiones catalysed by trifluoro acetic acid under solvent-free conditions. Chinese Chem. Lett., 20 (9), 1059- 1061.
18. Suzuki I., Suzumura Y., Takeda K. (2006) Metal triflimide as a Lewis acid Catalyst for Biginelli reactions in water. Tetrahedron Lett. 47(45), 7861-7864.
19. Singh K., Singh S., Kaur P. (2006) Efficacious preparation of Biginelli compounds. A comparative study of different reaction techniques. Letters in Org. Chem. 3(3), 201-203.
20. Zeng L.-Y., and Cai C. (2010) Ioine catalyzed one-pot multicomponent synthesis of a library of compounds containing tetrazolo [1, 5-a] pyrimidine Core. J. Comb. Chem., 12, 35–40.
21. Fedorova O. V., Zhidovinova M. S., Rusinov G. L., and Ovchinnikova I. G. (2003) Aminoazoles in the three component synthesis of 7-substituted 6-ethoxycarbonyl-5-methyl-4,7-dihydroazolo[1,5a]Pyrimidines, Russian Chem. Bull., Int. Ed., 52, 1768-1769.
22. Yao C., Lei S., Wang C., Yu C., and Tu S. (2008) Solvent-free Synthesis of 5-methyl-7-aryl-4,7-dihydrotetrazolo[1,5-a]pyrimidine-6-carboxylic esters Catalyzed by Sulfamic acid, J. Heterocyclic Chem., 45, 1609.
23. Chitra S., Devanathan D., and Pandiarajan K. (2010) Synthesis and in vitro Microbiological evaluation of novel 4-aryl-5-isopropoxycarbonyl-6-methyl-3,4-dihydropyrimidinones, European journal of medicinal Chemistry, 45, 367–371.
2. Kappe C. O. (1993) 100 years of the biginelli dihydropyrimidine synthesis. Tetrahedron, 49, 6937.
3. Gein V. L., Mishunin V. V., Tsyplyakova E. P., Vinokurova O. V., and M. I. Vakhrin (2009) Synthesis and antimicrobial activity of methyl-7-aryl(heteryl)-6-(2-thienoyl)-4,7-Dihydrotetrazolo[1,5-a]pyrimidine-5-carboxylates. Pharmaceutical Chemistry Journal. 43, 12.
4. Atwal K. S., Swanson B. N., Unger S. E., Floyd D. M., Moreland S., Hedberg A., and O’Reilly, B. C. (1991) Dihydropyrimidine calcium channel blockers. 3.3-Carbamoyl-4-aryl-1, 2, 3, 4-tetrahydro-6-methyl-5-pyrimidinecarboxylic acid esters as orally effective antihypertensive agents. J. Med. Chem. 34, 806-811.
5. Grover G. J., Dzwonczyk S., McMullen D. M., Normandin D.E., Parham C. S., Sleph P. G., and Moreland S. (1995) Pharmacologic Profile of the Dihydropyrimidine Calcium Channel Blockers SQ 32,547 and SQ 32, 946. J. Cardiovasc. Pharmacol. 26, 289.
6. Dallinger D., and Kappe O. (2007) Rapid preparation of the mitotic kinesin Eg5 inhibitor monastrol using controlled microwave-assisted synthesis. Nature protocols, 2, 317.
7. Snider B. B., and Shi Z. (1993) Biomimetic Synthesis of (±)-Crambines A, B, C1, and C2. Revision of the Structure of Crambines B and C1. J. Org. Chem., 58, 3828.
8. Overman L. E., Rabinowitz M. H., and Renhowe P. A. (1995) J. Am.Chem. Soc., 117, 2657.
9. Aly A. (2006) Synthesis and pharmacological activity of annelated pyrimidine derivatives. Phosphorus, Sulfur Silicon Relat. Elem., 181, 1285.
10. Ismail M. A. H., Aboul-Einein M. N. Y., Abouzid K. A. M., and Kandil S. B. A. (2002) Synthesis of Certain 5,6,7,8-tetrahydrobenzo[b]thienopyrimidines Fused with Various Heterocyclic Ring Systems as Potential Antihypertensive Agents. Alex. J. Pharm. Sci., 15, 143.
11. Drizin I., Holladay M. W., Yi L., Zhang H. Q., Gopalakrishnan S.,Gopalakrishnan M., Whiteaker K. L., Buckner S.A., Sullivan J. P., Carroll W. (2002) Bioorg. Med. Chem. Lett., 12, 1481.
12. Nagai S. I., Ueda T., Sugiura S., Nagatsu A., Murakami N., Sakakibara J., Fujita M., and Hotta Y. (1998). Synthesis and central nervous system stimulant activity of 5,8-methanoquinazolines fused with 1,2,4-triazole, tetrazoleand 1,2,4-triazine J. Heterocyclic Chem., 35, 325.
13. Ranu B. C., Hajra A., and Jana U. (2000) Indium (III) chloride-catalyzed one-pot synthesis of dihydropyrimidinones by a three-component coupling of 1,3-dicarbonyl compounds, aldehydes, and urea: an improved procedure for the biginelli reaction. J. Org. Chem., 65, 6270-6276.
14. Paraskar A. S., Dewker G. K., and Sudalai A. (2003) Cu (OTf)2: a reusable catalyst for high-yield synthesis of 3,4-dihydropyrimidin-2(1H)-ones. Tetrahedron Lett., 44, 3305-3308.
15. Raju C., Uma R., Kalaipriya M., Sridhar R., Ramakrishna S. (2011) Ammonium trifluoro acetate mediated synthesis of 3, 4-dihydropyrimidin-2(1H)-ones. ISRN Organic Chemistry, doi:10.5402/2011/273136.
16. Saha S., and Moorthy J. N. (2011) Enantioselective organocatalytic biginelli reaction: Dependence of the catalyst on sterics, hydrogen bonding, and reinforced chirality. J. Org. Chem., 76 (2), 396-402.
17. Shobha D., Adharvana Chari M., and Ahn K. H. (2009) An efficient biginelli one-pot synthesis of new benzoxazole-substituted dihydropyrimidinones and thiones catalysed by trifluoro acetic acid under solvent-free conditions. Chinese Chem. Lett., 20 (9), 1059- 1061.
18. Suzuki I., Suzumura Y., Takeda K. (2006) Metal triflimide as a Lewis acid Catalyst for Biginelli reactions in water. Tetrahedron Lett. 47(45), 7861-7864.
19. Singh K., Singh S., Kaur P. (2006) Efficacious preparation of Biginelli compounds. A comparative study of different reaction techniques. Letters in Org. Chem. 3(3), 201-203.
20. Zeng L.-Y., and Cai C. (2010) Ioine catalyzed one-pot multicomponent synthesis of a library of compounds containing tetrazolo [1, 5-a] pyrimidine Core. J. Comb. Chem., 12, 35–40.
21. Fedorova O. V., Zhidovinova M. S., Rusinov G. L., and Ovchinnikova I. G. (2003) Aminoazoles in the three component synthesis of 7-substituted 6-ethoxycarbonyl-5-methyl-4,7-dihydroazolo[1,5a]Pyrimidines, Russian Chem. Bull., Int. Ed., 52, 1768-1769.
22. Yao C., Lei S., Wang C., Yu C., and Tu S. (2008) Solvent-free Synthesis of 5-methyl-7-aryl-4,7-dihydrotetrazolo[1,5-a]pyrimidine-6-carboxylic esters Catalyzed by Sulfamic acid, J. Heterocyclic Chem., 45, 1609.
23. Chitra S., Devanathan D., and Pandiarajan K. (2010) Synthesis and in vitro Microbiological evaluation of novel 4-aryl-5-isopropoxycarbonyl-6-methyl-3,4-dihydropyrimidinones, European journal of medicinal Chemistry, 45, 367–371.