N-Substituted benzoxazolyl ureas and thioureas in Biginelli reaction promoted by trifluoromethane sulfonic acid: An efficient and convenient synthesis of substituted benzoxazolyl 3,4-dihydropyrimidine (1H)-(thio)-ones

作者: M. Saranga Pani , M. Arjun , D. Sridhar , K. Srinivas , T. Raviprasad

DOI: 10.1016/J.CCLET.2009.04.010

关键词:

摘要: Abstract An efficient synthesis of 3,4-dihydropyrimidine 2 (1 H )-ones and thiones (3,4-DHPMs) core was prepared by one-pot three-component Biginelli condensation which catalyzed trifluoromethane sulfonic acid. The classical Bignelli reaction has been extended the use N-substituted benzoxazolyl semicarbazides thiosemicarbazides this method advantage excellent yields short times.

参考文章(17)
C. Oliver Kappe, 100 years of the biginelli dihydropyrimidine synthesis Tetrahedron. ,vol. 49, pp. 6937- 6963 ,(1993) , 10.1016/S0040-4020(01)87971-0
Armido Studer, Patrick Jeger, Peter Wipf, Dennis P. Curran, Fluorous Synthesis: Fluorous Protocols for the Ugi and Biginelli Multicomponent Condensations Journal of Organic Chemistry. ,vol. 62, pp. 2917- 2924 ,(1997) , 10.1021/JO970095W
George C. Rovnyak, S. David Kimball, Barbara Beyer, Gabriella Cucinotta, John D. DiMarco, Jack Gougoutas, Anders Hedberg, Mary Malley, James P. McCarthy, Calcium entry blockers and activators: conformational and structural determinants of dihydropyrimidine calcium channel modulators. Journal of Medicinal Chemistry. ,vol. 38, pp. 119- 129 ,(1995) , 10.1021/JM00001A017
George C. Rovnyak, Karnail S. Atwal, Anders Hedberg, S. David Kimball, Suzanne Moreland, Jack Z. Gougoutas, Brian C. O'Reilly, Joseph Schwartz, Mary F. Malley, Dihydropyrimidine calcium channel blockers. 4. Basic 3-substituted-4-aryl-1,4-dihydropyrimidine-5-carboxylic acid esters. Potent antihypertensive agents. Journal of Medicinal Chemistry. ,vol. 35, pp. 3254- 3263 ,(1992) , 10.1021/JM00095A023
Hidetsura Cho, Masaru Ueda, Keiyuu Shima, Akira Mizuno, Mariko Hayashimatsu, Yoshiko Ohnaka, Yumi Takeuchi, Mikiko Hamaguchi, Kazuo Aisaka, Dihydropyrimidines: novel calcium antagonists with potent and long-lasting vasodilative and antihypertensive activity. Journal of Medicinal Chemistry. ,vol. 32, pp. 2399- 2406 ,(1989) , 10.1021/JM00130A029
Barry B. Snider, Zhongping Shi, Biomimetic synthesis of (.+-.)-crambines A, B, C1, and C2. Revision of the structure of crambines B and C1 Journal of Organic Chemistry. ,vol. 58, pp. 3828- 3839 ,(1993) , 10.1021/JO00067A014
Karnail S. Atwal, Brian N. Swanson, Steven E. Unger, David M. Floyd, Suzanne Moreland, Anders Hedberg, Brian C. O'Reilly, 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. Journal of Medicinal Chemistry. ,vol. 34, pp. 806- 811 ,(1991) , 10.1021/JM00106A048