Efficient Synthesis of New Stable 1,4-diionic Organosulfurs and Corresponding Mesoionic Compounds from N-Heterocyclic Ylides
作者： Fahimeh Shahrekipour , Reza Heydari , Batool Tahamipour , Hamideh Saravani , Claudia Graiff
DOI: 10.1080/10426507.2013.819866
关键词: Mesoionic 、 Triethylamine 、 Dehydrogenation 、 Organosulfur compounds 、 Organic chemistry 、 Chemistry 、 Isothiocyanate 、 1,3-Dipolar cycloaddition 、 Pyridinium 、 Sulfur
摘要: Abstract N-Phenacyl heterocyclic salts such as isoquinolinium, quinolinium, and pyridinium bromide react quickly with benzoyl isothiocyanate in the present of triethylamine to produce 1,4-diionic organosulfur derivatives. Cyclization dehydrogenation organosulfurs gave thiazoloisoquinolinium, or benzimidates. [Supplementary materials are available for this article. Go publisher's online edition Phosphorus, Sulfur, Silicon Related Elements following free supplemental files: Figures.].
sci-hub.se 参考文章(34)
Hemant Panwar, Shishupal Singh, Nidhi Chaudhary, SYDNONE DERIVATIVES A SYNTHONS FOR NOVEL MESOIONIC COMPOUNDS. SYNTHESIS, CHARACTERIZATION AND ANTIMICROBIAL EVALUATION OF SOME 2-(4`-SUBSTITUTED ANILINOSYNDON-3`-YL)-1, 3, 4-THIADIAZINO (6, 5-B) INDOLES Indonesian Journal of Chemistry. ,vol. 11, pp. 201- 206 ,(2011) , 10.22146/IJC.21380
Masami Kawase, Hiroshi Sakagami, Noboru Motohashi, The Chemistry of Bioactive Mesoionic Heterocycles Bioactive Heterocycles VII. ,vol. 16, pp. 135- 152 ,(2007) , 10.1007/7081_2007_096
A.A. F. Wasfy, Studies on Quinazolines. Part III. Synthesis of Some Fused-Ring Cationic and Mesoionic Derivatives of the 1,3-Thiazolo[3,2-c]quinazoline Ring System Phosphorus Sulfur and Silicon and The Related Elements. ,vol. 178, pp. 1901- 1910 ,(2003) , 10.1080/10426500390221078
K. Satyanarayana, M.N.A. Rao, Synthesis and antiinflammatory, analgesic, and antipyretic testing of 4-[1-oxo-(3-substituted aryl)-2-propenyl]-3-phenylsydnones and of 3-[4-[3-(substituted aryl)-1-oxo-2-propenyl]phenyl]sydnones Journal of Pharmaceutical Sciences. ,vol. 84, pp. 263- 266 ,(1995) , 10.1002/JPS.2600840228
Magali B. De Oliveira, Joseph Miller, Arnaldo B. Pereira, Sérgio E. Galembeck, Gustavo L. C. De Moura, Alfredo M. Simas, Mesoionic 2-n-cycloalkylamino-5-alkyl-1,3-dithiolium-4-thiolates Phosphorus Sulfur and Silicon and The Related Elements. ,vol. 108, pp. 75- 84 ,(1996) , 10.1080/10426509608029640
John E. Baldwin, Mildred C. McDaniel, M.Gary Newton, Iain C. Paul, The structure of the adduct from N-[-bromobenzyl]-isoquinolinium bromide and carbon disulfide Tetrahedron Letters. ,vol. 7, pp. 4239- 4241 ,(1966) , 10.1016/S0040-4039(00)76043-6
K. V. Fedotov, T. P. Shumeiko, N. N. Romanov, A. I. Tolmachev, A. Ya. Ilchenko, Cyclization of substituted (2-pyridylthio)phenylacetic acids and chromaticity of mesoionic thiazolo[3,2-a]pyridinium-3-olates Chemistry of Heterocyclic Compounds. ,vol. 47, pp. 622- 630 ,(2011) , 10.1007/S10593-011-0807-Z
Wing Lai Chan, Chok Wah Lo, Yau Shan Szeto, Chiu Wing Yip, Synthesis of Polycyclic Bismesoionic Compounds HETEROCYCLES. ,vol. 51, pp. 1433- 1436 ,(1999) , 10.3987/COM-99-8507
Martín Ávalos, Reyes Babiano, Pedro Cintas, Jesús Díaz, José L. Jiménez, Ignacio López, Juan C. Palacios, Non-Dipolar Behavior of Mesoionic Heterocycles: Synthesis and Tautomerism of 2-Alkylthioisomünchnones European Journal of Organic Chemistry. ,vol. 2004, pp. 2805- 2811 ,(2004) , 10.1002/EJOC.200400049
Cledualdo Soares de Oliveira, Bruno Freitas Lira, Vivyanne dos Santos Falcão-Silva, Jose Pinto Siqueira-Junior, Jose Maria Barbosa-Filho, Petronio Filgueiras de Athayde-Filho, Synthesis, molecular properties prediction, and anti-staphylococcal activity of N-acylhydrazones and new 1,3,4-oxadiazole derivatives. Molecules. ,vol. 17, pp. 5095- 5107 ,(2012) , 10.3390/MOLECULES17055095