Chalcone derivatives were synthesis by the reaction of some 4-nitrobenzaldehyde derivatives with acotophenone then the product obtained E-3-(4-nitrophenyl)-1-phenylprop-2-en-1-one. This product is chalcone is another react with guanidine nitrate. The hetrocyclic derivatives of guanidine nitrate respectively the final product have been characterized by elemental analysis. the product obtained is 1,6 dihydro 6(4-nitrophenyl) 4-phenylpyridine 2-amine. In present report novel pyrimidines were prepared from starting materials chalcone and guanidine nitrate. The resulting compound 1,6-dihydro-6-(4-nitrophenyl)-4 phenylpyrimidin 2 amine (2) was further reacted with 2 bis(methylthio)methylene malononitrile in the presence of catalytic amount of potassium carbonate in DMF under reflux condition that offered novel 4,6,9,9a-tetrahydro-4-imino-2-(methylthio)-8-(4-nitrophenyl) 6 phenyl 1H pyrimido[1,2 a]pyrimidine 3 carbonitrile (3). The synthesized compounds were characterized by spectral methods. The compound (3) possesses replaceable methylthio (-SCH3) group at 2 position. The compound (3) react with various nucleophiles like substituted aromatic amines, aromatic phenols, hetryl amines and active methylene compounds to give 4,6,9,9a-tetrahydro-4-imino-2-(methylthio)-8-(4-nitrophenyl)-6-phenyl-1H-pyrimido[1,2-a]pyrimidine-3-carbonitrile –carbonitrile in good yields.
Published in | International Journal of Pharmacy and Chemistry (Volume 6, Issue 1) |
DOI | 10.11648/j.ijpc.20200601.11 |
Page(s) | 1-5 |
Creative Commons |
This is an Open Access article, distributed under the terms of the Creative Commons Attribution 4.0 International License (http://creativecommons.org/licenses/by/4.0/), which permits unrestricted use, distribution and reproduction in any medium or format, provided the original work is properly cited. |
Copyright |
Copyright © The Author(s), 2020. Published by Science Publishing Group |
Claisen Schmidt Condensation, 2 bis(methylthio)methylene malononitrile Michael Addition Reaction, Pyrimidine
[1] | Devprakash, AB Udaykumar, Journal of Pharmaceutical Research, 2011; 4 (7): 2436-2440. |
[2] | T. Sasada, F. Kobayashi, N. Sakai, T. Konakahara, Organic Letters, 2009; 11: 2161-2164. |
[3] | FL Rodney, G Charles, Skinner, S William, Canadian Journal of Chemistry, 1967; 45: 2213-2216. |
[4] | VP Litvinov, Advances in Heterocyclic Chemistry, vol. 92, Zelinsky Institute of Organic chemistry, Russian Academy of Sciences, 119991 Moscow, Russia, 2006; 83. |
[5] | Amir M, Javed SA and Kumar H; Indian J. Pharm. Sciences, 2007; 69 (3): 337-343. |
[6] | O Stanisaw, (2009), some biologically active pyrimidine derivatives are prazosin, quinethazone trimethotrexate, folic acid, riboflavin, Jord. J. Chem, 4: 1-15. |
[7] | Jain MK, Sharnevas SC; Organic Chem.; 2008; 3; 997-999. |
[8] | Desai K, Patel R, Chikhalia K. J Ind Chem, 2006; 45: 773-778. |
[9] | Amr EA, Nermien MS, Abdulla MM. Monatsh Chem, 2007; 138: 699-707. |
[10] | Fujiwara N, Nakajima T, Ueda Y, Fujita HK, Awakami H. Bioorg Med Chem, 2008; 16: 9804-9816. |
[11] | Ballell L, Field RA, Chung GAC, Young RJ. Bioorg Med Chem Lett, 2007; 17: 1736-1740. |
[12] | Wagner E, Al-Kadasi K, Zimecki M, Sawka-Dobrowolska W. Eur J Med Chem, 2008; 43: 2498-2504. |
[13] | Jean-Damien C, David B, Ronald K, Julian G, Pan L, Robert D. Vertex Pharmaceuticals Incorporated, USA, PCT Int. Appl. 2002; 22: 608. |
[14] | Gorlitzer K, Herbig S, Walter RD. Pharmazie, 1997; 52: 670-672. |
[15] | Ukrainets IV, Tugaibei IA, Bereznykova NL, Karvechenko VN, Turov AV. Khimiya Geterotsiklicheskikh Soedinenii, 2008; 5: 718-729. |
[16] | Kurono M, Hayashi M, Miura K, Isogawa Y, Sawai K, Kokai Tokkyo Koho JP 1987; 62: 267-272, Chem. Abstr, 1988; 109: 37832. |
[17] | Wang SQ, Fang L, Liu XJ, Zhao K. Chinese Chem Lett, 2004; 15: 885-888. |
[18] | Yang W, Ruan Z, Wang Y, Van Kirk K, Ma Z, Arey BJ. et al. J Med Chem, 2009; 52: 1204-1208. |
[19] | Gillespie RJ, Bamford SJ, Botting R, Comer M, Denny S, et al. J Med Chem, 2009; 52: 33-47 |
[20] | A Hausen, D Fuchs, G Reibnegger, H Wachter, Cancer, 1984, 53 (7), 1634-6. |
[21] | T Netzer, F Ullrich, H Priewer, M Majewski, E Mutschler, Brit. J. Pharmac, 1992; 106 (1): 222–226. |
[22] | Y Zheng, M Sun, Y Liu, M Li, M Ji, Med. Chem, 2011; 7 (4): 295-300. |
[23] | K Sushil, Kashaw, G Vivek, K Varsha, P Mishra, JP Stables, NK Jain, Med. Chem. Research, 2010; 19: 250-261. |
[24] | DW Combs, MS Rampulla, RK Russell, RA Rampulla, DH Klaubert, D Ritchie, AS Meeks, T Kirchner, Drug Design Delivery, 1990; 6 (4): 241-254. |
[25] | AR Katritzky, CW Rees, EFV Scriven, Comprehensive Heterocyclic Chemistry II, Boulton, A. J., Ed., 6, Pergamon Press: Oxford – New York – Tokyo, 1996; 195-231. |
[26] | G Jian, Z Quan, ON Michael, O Nicanor, A Arba, G Lucia, AJ Lin, Antimicrobial Agents and Chemotherapy, 2005; 49: 4928-4933. |
[27] | O Stanisaw, Jord. J. Chem, 2009; 4: 1-15. |
APA Style
Sirsat Shivraj Balajirao, Jadhav Anilkumar Govindrao, Nilesh B Chavhan. (2020). Synthesis of Novel Pyrimido Pyrimidine and Their Derivatives. International Journal of Pharmacy and Chemistry, 6(1), 1-5. https://doi.org/10.11648/j.ijpc.20200601.11
ACS Style
Sirsat Shivraj Balajirao; Jadhav Anilkumar Govindrao; Nilesh B Chavhan. Synthesis of Novel Pyrimido Pyrimidine and Their Derivatives. Int. J. Pharm. Chem. 2020, 6(1), 1-5. doi: 10.11648/j.ijpc.20200601.11
AMA Style
Sirsat Shivraj Balajirao, Jadhav Anilkumar Govindrao, Nilesh B Chavhan. Synthesis of Novel Pyrimido Pyrimidine and Their Derivatives. Int J Pharm Chem. 2020;6(1):1-5. doi: 10.11648/j.ijpc.20200601.11
@article{10.11648/j.ijpc.20200601.11, author = {Sirsat Shivraj Balajirao and Jadhav Anilkumar Govindrao and Nilesh B Chavhan}, title = {Synthesis of Novel Pyrimido Pyrimidine and Their Derivatives}, journal = {International Journal of Pharmacy and Chemistry}, volume = {6}, number = {1}, pages = {1-5}, doi = {10.11648/j.ijpc.20200601.11}, url = {https://doi.org/10.11648/j.ijpc.20200601.11}, eprint = {https://article.sciencepublishinggroup.com/pdf/10.11648.j.ijpc.20200601.11}, abstract = {Chalcone derivatives were synthesis by the reaction of some 4-nitrobenzaldehyde derivatives with acotophenone then the product obtained E-3-(4-nitrophenyl)-1-phenylprop-2-en-1-one. This product is chalcone is another react with guanidine nitrate. The hetrocyclic derivatives of guanidine nitrate respectively the final product have been characterized by elemental analysis. the product obtained is 1,6 dihydro 6(4-nitrophenyl) 4-phenylpyridine 2-amine. In present report novel pyrimidines were prepared from starting materials chalcone and guanidine nitrate. The resulting compound 1,6-dihydro-6-(4-nitrophenyl)-4 phenylpyrimidin 2 amine (2) was further reacted with 2 bis(methylthio)methylene malononitrile in the presence of catalytic amount of potassium carbonate in DMF under reflux condition that offered novel 4,6,9,9a-tetrahydro-4-imino-2-(methylthio)-8-(4-nitrophenyl) 6 phenyl 1H pyrimido[1,2 a]pyrimidine 3 carbonitrile (3). The synthesized compounds were characterized by spectral methods. The compound (3) possesses replaceable methylthio (-SCH3) group at 2 position. The compound (3) react with various nucleophiles like substituted aromatic amines, aromatic phenols, hetryl amines and active methylene compounds to give 4,6,9,9a-tetrahydro-4-imino-2-(methylthio)-8-(4-nitrophenyl)-6-phenyl-1H-pyrimido[1,2-a]pyrimidine-3-carbonitrile –carbonitrile in good yields.}, year = {2020} }
TY - JOUR T1 - Synthesis of Novel Pyrimido Pyrimidine and Their Derivatives AU - Sirsat Shivraj Balajirao AU - Jadhav Anilkumar Govindrao AU - Nilesh B Chavhan Y1 - 2020/04/30 PY - 2020 N1 - https://doi.org/10.11648/j.ijpc.20200601.11 DO - 10.11648/j.ijpc.20200601.11 T2 - International Journal of Pharmacy and Chemistry JF - International Journal of Pharmacy and Chemistry JO - International Journal of Pharmacy and Chemistry SP - 1 EP - 5 PB - Science Publishing Group SN - 2575-5749 UR - https://doi.org/10.11648/j.ijpc.20200601.11 AB - Chalcone derivatives were synthesis by the reaction of some 4-nitrobenzaldehyde derivatives with acotophenone then the product obtained E-3-(4-nitrophenyl)-1-phenylprop-2-en-1-one. This product is chalcone is another react with guanidine nitrate. The hetrocyclic derivatives of guanidine nitrate respectively the final product have been characterized by elemental analysis. the product obtained is 1,6 dihydro 6(4-nitrophenyl) 4-phenylpyridine 2-amine. In present report novel pyrimidines were prepared from starting materials chalcone and guanidine nitrate. The resulting compound 1,6-dihydro-6-(4-nitrophenyl)-4 phenylpyrimidin 2 amine (2) was further reacted with 2 bis(methylthio)methylene malononitrile in the presence of catalytic amount of potassium carbonate in DMF under reflux condition that offered novel 4,6,9,9a-tetrahydro-4-imino-2-(methylthio)-8-(4-nitrophenyl) 6 phenyl 1H pyrimido[1,2 a]pyrimidine 3 carbonitrile (3). The synthesized compounds were characterized by spectral methods. The compound (3) possesses replaceable methylthio (-SCH3) group at 2 position. The compound (3) react with various nucleophiles like substituted aromatic amines, aromatic phenols, hetryl amines and active methylene compounds to give 4,6,9,9a-tetrahydro-4-imino-2-(methylthio)-8-(4-nitrophenyl)-6-phenyl-1H-pyrimido[1,2-a]pyrimidine-3-carbonitrile –carbonitrile in good yields. VL - 6 IS - 1 ER -