Synthesis of [(4-chloro-5H-1,2,3-dithiazol-5-ylidene)amino]azines.
نویسندگان
چکیده
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.
منابع مشابه
The 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 کاملA 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.
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 ...
متن کاملFused 1,2,3-Dithiazoles: Convenient Synthesis, Structural Characterization, and Electrochemical Properties.
A new general protocol for synthesis of fused 1,2,3-dithiazoles by the reaction of cyclic oximes with S₂Cl₂ and pyridine in acetonitrile has been developed. The target 1,2,3-dithiazoles fused with various carbocycles, such as indene, naphthalenone, cyclohexadienone, cyclopentadiene, and benzoannulene, were selectively obtained in low to high yields. In most cases, the hetero ring-closure was ac...
متن کاملMethyl 1-[(Z)-2-(benzyloxycarbonyl)hydrazin-1-ylidene]-5-chloro-2-hydroxyindane-2-carboxylate
The title compound, C19H17ClN2O5, is an important inter-mediate for the synthesis of the pesticide Indoxacarb [systematic name: (S)-methyl 7-chloro-2-{[(meth-oxy-carbon-yl)[4-(tri-fluoro-meth-oxy)phen-yl]amino]-carbon-yl}-2H,3H,4aH,5H-indeno-[1,2-e][1,3,4]oxadiazine-4a-carboxyl-ate] The C=N double bond has a Z conformation. An intra-molecular N-H⋯O hydrogen bond occurs. In the crystal structure...
متن کاملThe 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 کاملذخیره در منابع من
با ذخیره ی این منبع در منابع من، دسترسی به آن را برای استفاده های بعدی آسان تر کنید
برای دانلود متن کامل این مقاله و بیش از 32 میلیون مقاله دیگر ابتدا ثبت نام کنید
ثبت ناماگر عضو سایت هستید لطفا وارد حساب کاربری خود شوید
ورودعنوان ژورنال:
- Molecules
دوره 16 11 شماره
صفحات -
تاریخ انتشار 2011