In present report novel thiazines were prepared from starting materials chalcone and thiourea. The resulting compound 6-(4-methoxyphenyl) 4-phenyl-6H-1, 3-thiazin-2-amine (2) was further reacted with ethyl 2-cyano-3, 3-bis (methylthio) acrylate in the presence of catalytic amount of potassium carbonate in DMF under reflux condition that offered novel 2-(4-methoxyphenyl) 8-(methylthio)-6-0xo-4-phenyl-4, 6, 9, 9a-tetrahydropyrimido [2, 1-b] [1, 3]-thiazine-7-carbonitrile (3). The synthesized compounds were characterized by spectral methods. The compound (3) possesses replaceable methylthio (-SCH3) group at 8 position. The compound (3) react with various nucleophiles like substituted aromatic amines, aromatic phenols, hetryl amines and active methylene compounds to give 2-(4-methoxyphenyl)-8-substituted-6-oxo-4-phenyl-4, 6, 9, 9a-tetrahydropyrimido [2, 1-b] [1, 3] thiazine-7-carbonitrile in good yields.
| Published in | American Journal of Heterocyclic Chemistry (Volume 5, Issue 2) |
| DOI | 10.11648/j.ajhc.20190502.11 |
| Page(s) | 23-26 |
| 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), 2019. Published by Science Publishing Group |
Claisen-Schmidt Condensation, 2-Cyano-3, 3-Bis (Methylthio) Acrylate,Michael Addition Reaction, Thiazines
| [1] | H. Joshi, P. Upadhyay, A. J Baxi, J. Indian Chem. Soc., 67, 779 (1990). |
| [2] | S. P. Rathod, A. P. Charjan and P. R. Rajput, Synthesis and Antibacterial Activities of Chloro-Substituted-1, 3-Thiazines, Rasayn J. Chem., 2010. |
| [3] | C. Sanjeeva Reddy and A. Nagaraj, Synthesis and Biological Study of Novel Bis-chalcones, Bis-Thiazines and Bis-pyrimidines, J. Iran. Chem. Soc., Vol.5, No.2, June 2008, 262-267. |
| [4] | Mamoru Kokestu, Kohsuke Tanaka, Yuichi Takenaka, Cecil D, Kwong and Hideharu Ishihara, Synthesis of 1, 3-thiazine derivatives and their evaluation as potential antimycobacterial agents, European j pharm. Sci., April 2002, volume 15, Issue 3, Pg. no. 307-310. |
| [5] | R. Kalirajan, S. U. Sivakumar, S. Jubie, B. Gowramma and B. Suresh, Internl. J. Chem Tech Res., Jan –March 2009, Vol 1, No.1, 27-34. |
| [6] | Tojkoporan, Synthesis of some 1, 2, 4-triazolo [3, 2-b]-1, 3-thiazine-7-ones with potential analgesic and anti-inflammatory activities, pubmed, 2002 Feb; 57 (2), 145-52. |
| [7] | Li Fu, Li Fu, Ding Ye, Ying Li and Shufan Yin, Synthesis and claiming activity of 6H-2-Amino-4-Aryl-6-(4-b-D-Allopyranosyloxyphenyl)-1, 3-thiazine, Chemistry of natural products, vol.46, no.2, 169-172. |
| [8] | Zawisza, Synthesis and pharmacological analysis of new derivatives of tetrahydro-[1, 3]-thiazine and 2-thiobarbituric acid, National center for biotechnology information, 1981; 29 (2), 235-48. |
| [9] | Jin Guiyu Cao Chunyang, Synthesis and biological activities of substituted pyrazolo [4, 5 e] [1, 3] thiazine derivatives, Chinese journal of pesticide science, 1981; 29 (2), Pg. no.; 235-48. |
| [10] | Diurno M V, Mazzoni O, Piscopo E, Calignano A, Giordano F, and Bolognese A 1992 J. Med. Chem. 35 2910. |
| [11] | Rawal R K, Tripathi R, Katti S B, Pannecouque C and DeClercq E 2007 Bioorg. Med. Chem. 15 3134. |
| [12] | (a) Ottana R K, Carroti S, Maccari R, Landini I, Chiricosta G, Caciagli B, Vigorita M G and Mini E 2005 Bioorg. Med. Chem. Lett. 15 3930; (b) Gududuru V, Hurh E, Dalton J T and Miller D D 2004 Bioorg. Med. Chem. Lett. 14 5289. |
| [13] | Campaigne E and Nargund P K 1964 J. Org. Chem. 29 224. |
| [14] | Dana W. Mayo, Ronald M. Pike, David C. Forbes; Microscale Organic Labor-atory; with Multistep and Multiscale Synthesis, (2010) 308-310. |
| [15] | S. V. Kostanecki, Tambor; J. Chem. Ber., 32, 1921 (1899). |
| [16] | Jain AC, Prasad AK (1995) Reaction of chalcone 2-4,-dimethoxychalcone, a-bromo and methoxy chalcone with thiourea. Indian J Chem 34B: 496. 14. |
| [17] | Sambhaji PV, Vijay NB, Sandeep V. Khansole, Ramdas NK (2009) A convenient one pot synthesis of 3-cyano-9-methyl-2-methylthio-4-0xo-4H-pyrimidi-[2, 1-b] [4, 5-b] quinolone and its reaction with selected nucleophiles. Letters in organic chemistry 6: 544-548. |
APA Style
Sirsat Shivraj Balajirao, Jadhav Anilkumar Govindrao, Kale Prashant Sambharao, Jadhav Madhav Sopanrao. (2019). Synthesis of Novel Pyrimido Thiazine and Their Derivatives. American Journal of Heterocyclic Chemistry, 5(2), 23-26. https://doi.org/10.11648/j.ajhc.20190502.11
ACS Style
Sirsat Shivraj Balajirao; Jadhav Anilkumar Govindrao; Kale Prashant Sambharao; Jadhav Madhav Sopanrao. Synthesis of Novel Pyrimido Thiazine and Their Derivatives. Am. J. Heterocycl. Chem. 2019, 5(2), 23-26. doi: 10.11648/j.ajhc.20190502.11
AMA Style
Sirsat Shivraj Balajirao, Jadhav Anilkumar Govindrao, Kale Prashant Sambharao, Jadhav Madhav Sopanrao. Synthesis of Novel Pyrimido Thiazine and Their Derivatives. Am J Heterocycl Chem. 2019;5(2):23-26. doi: 10.11648/j.ajhc.20190502.11
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Download@article{10.11648/j.ajhc.20190502.11,
author = {Sirsat Shivraj Balajirao and Jadhav Anilkumar Govindrao and Kale Prashant Sambharao and Jadhav Madhav Sopanrao},
title = {Synthesis of Novel Pyrimido Thiazine and Their Derivatives},
journal = {American Journal of Heterocyclic Chemistry},
volume = {5},
number = {2},
pages = {23-26},
doi = {10.11648/j.ajhc.20190502.11},
url = {https://doi.org/10.11648/j.ajhc.20190502.11},
eprint = {https://article.sciencepublishinggroup.com/pdf/10.11648.j.ajhc.20190502.11},
abstract = {In present report novel thiazines were prepared from starting materials chalcone and thiourea. The resulting compound 6-(4-methoxyphenyl) 4-phenyl-6H-1, 3-thiazin-2-amine (2) was further reacted with ethyl 2-cyano-3, 3-bis (methylthio) acrylate in the presence of catalytic amount of potassium carbonate in DMF under reflux condition that offered novel 2-(4-methoxyphenyl) 8-(methylthio)-6-0xo-4-phenyl-4, 6, 9, 9a-tetrahydropyrimido [2, 1-b] [1, 3]-thiazine-7-carbonitrile (3). The synthesized compounds were characterized by spectral methods. The compound (3) possesses replaceable methylthio (-SCH3) group at 8 position. The compound (3) react with various nucleophiles like substituted aromatic amines, aromatic phenols, hetryl amines and active methylene compounds to give 2-(4-methoxyphenyl)-8-substituted-6-oxo-4-phenyl-4, 6, 9, 9a-tetrahydropyrimido [2, 1-b] [1, 3] thiazine-7-carbonitrile in good yields.},
year = {2019}
}
TY - JOUR T1 - Synthesis of Novel Pyrimido Thiazine and Their Derivatives AU - Sirsat Shivraj Balajirao AU - Jadhav Anilkumar Govindrao AU - Kale Prashant Sambharao AU - Jadhav Madhav Sopanrao Y1 - 2019/06/29 PY - 2019 N1 - https://doi.org/10.11648/j.ajhc.20190502.11 DO - 10.11648/j.ajhc.20190502.11 T2 - American Journal of Heterocyclic Chemistry JF - American Journal of Heterocyclic Chemistry JO - American Journal of Heterocyclic Chemistry SP - 23 EP - 26 PB - Science Publishing Group SN - 2575-5722 UR - https://doi.org/10.11648/j.ajhc.20190502.11 AB - In present report novel thiazines were prepared from starting materials chalcone and thiourea. The resulting compound 6-(4-methoxyphenyl) 4-phenyl-6H-1, 3-thiazin-2-amine (2) was further reacted with ethyl 2-cyano-3, 3-bis (methylthio) acrylate in the presence of catalytic amount of potassium carbonate in DMF under reflux condition that offered novel 2-(4-methoxyphenyl) 8-(methylthio)-6-0xo-4-phenyl-4, 6, 9, 9a-tetrahydropyrimido [2, 1-b] [1, 3]-thiazine-7-carbonitrile (3). The synthesized compounds were characterized by spectral methods. The compound (3) possesses replaceable methylthio (-SCH3) group at 8 position. The compound (3) react with various nucleophiles like substituted aromatic amines, aromatic phenols, hetryl amines and active methylene compounds to give 2-(4-methoxyphenyl)-8-substituted-6-oxo-4-phenyl-4, 6, 9, 9a-tetrahydropyrimido [2, 1-b] [1, 3] thiazine-7-carbonitrile in good yields. VL - 5 IS - 2 ER -
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