A Qualitative Comparison of the Reactivities of 3,4,4,5-Tetrachloro-4H-1,2,6-thiadiazine and 4,5-Dichloro-1,2,3-dithiazolium Chloride.
نویسندگان
چکیده
The high yielding transformations of 3,4,4,5-tetrachloro-4H-1,2,6-thiadiazine into 3,5-dichloro-4H-1,2,6-thiadiazin-4-one (up to 85%) and 2-(3,5-dichloro-4H-1,2,6-thiadiazin-4-ylidene)malononitrile (up to 83%) have been investigated and compared to the analogous transformations of the closely-related 4,5-dichloro-1,2,3-dithiazolium chloride (Appel's salt) into 4-chloro-5H-1,2,3-dithiazol-5-one and 2-(4-chloro-5H-1,2,3-dithiazol-5-ylidene)malononitrile. Furthermore, cyclocondensation of 3,4,4,5-tetrachloro-4H-1,2,6-thiadiazine with 2-aminophenol and 1,2-benzenediamines gave fused 4H-1,2,6-thiadiazines in 68%-85% yields.
منابع مشابه
The reaction of 4,5-dichloro-1,2,3-dithiazolium chloride with sulfimides: a new synthesis of N-aryl-1,2,3-dithiazolimines.
N-Aryl-S,S-dimethylsulfimides 3(Ar = 4-NO(2)C(6)H(4)), 4 (Ar = Ph) and 5 (Ar = 4-Tol)react with Appel salt 1 to give the corresponding N-aryl-(4-chloro-5H-1,2,3-dithiazolylidene)benzenamines 8 (Ar = 4-NO(2)C(6)H(4)), 9 (Ar = Ph) and 10 (Ar = 4-Tol) in 84, 94 and 87% yields, respectively. The reaction proceeds in the absence of base and a proposed reaction mechanism is given.
متن کاملSynthesis of [(4-chloro-5H-1,2,3-dithiazol-5-ylidene)amino]azines.
The reactions of 2-, 3- and 4-aminopyridines with 4,5-dichloro-1,2,3-dithiazolium chloride (Appel salt) 4 to give N-(4-chloro-5H-1,2,3-dithiazol-5-ylidene)pyridin-X-amines 1a (X = 2), 1g (X = 3) and 1k (X = 4) were optimized with respect to base, temperature and reaction time. Based on these conditions a total of thirteen [(dithiazolylidene)amino]azines 1a-m were prepared and fully characterized.
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Z. Naturforsch. 53 b, 532-534 (1998); received December 18, 1997 Crystal Structure, 1,2,6-Thiadiazines, Sulfanuric Chloride The title compound was obtained by the reaction of 3,5-dimethyl-2//-l,2,6-thiadiazine-l,ldioxide with PCI5 in chloroform. It crystallizes in the monoclinic system, space group P2\/c, a = 7.521(7) A, b = 8.400(4) A, c = 13.908(4) Ä, ß = 100.35(4)°, V = 864.4(8) A3, and Z = ...
متن کاملThe conversion of [(4-chloro-5H-1,2,3-dithiazol-5-ylidene)amino]azines into azine fused thiazole-2-carbonitriles.
The thermolysis of several N-(4-chloro-5H-1,2,3-dithiazol-5-ylidene)pyridin-n-amines (where n = 2, 3 and 4) gives a mixture of thiazolopyridine-2-carbonitriles in low to moderate yields. Introduction, by design, of a chlorine substituent at the C2 or C4 position of N-(4-chloro-5H-1,2,3-dithiazol-5-ylidene)pyridin-3-amine and other selected azines enables a BnEt(3)NI mediated ANRORC style ring t...
متن کاملSynthesis, characterization and polymerization of a novel acrylate monomer containing both 4H-pyran-4-one and 1,2,3-triazole moiety and evaluation of their antibacterial activity
A novel acrylate monomer containing 4H-pyran-4-one and 1,2,3-triazole ring, {1-[4-(4-oxo-6-phenyl-4H-pyran-2-yl)benzyl]-1,2,3-triazol-4-yl}methyl acrylate was synthesized by the reaction of 2-{4-[(4-(hydroxymethyl)-1,2,3-triazol-1-yl)methyl]phenyl}-6-phenyl-4H-pyran-4-one with acryloyl chloride in the presence of triethylamine. The structure of the acrylate monomer was established on the basis ...
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ورودعنوان ژورنال:
- Molecules
دوره 20 8 شماره
صفحات -
تاریخ انتشار 2015