Chemistry of Heterocyclic Compounds: Five Member by L. L. Bambas, Arnold Weissberger

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By L. L. Bambas, Arnold Weissberger

The Chemistry of Heterocyclic Compounds, given that its inception, has been famous as a cornerstone of heterocyclic chemistry. each one quantity makes an attempt to debate all facets – homes, synthesis, reactions, physiological and business importance – of a selected ring process. to maintain the sequence up to date, supplementary volumes overlaying the hot literature on every one person ring method were released. Many ring platforms (such as pyridines and oxazoles) are taken care of in detailed books, each one which include separate volumes or components facing assorted person subject matters. With all authors are famous specialists, the Chemistry of Heterocyclic Chemistry is taken into account all over the world because the fundamental source for natural, bioorganic, and medicinal chemists.

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Additional resources for Chemistry of Heterocyclic Compounds: Five Member Heterocyclic Compounds With Nitrogen and Sulfur or Nitrogen, Sulfur and Oxygen (Except Thiazole), Volume 4

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25, Ref. 799 (1892); Oefvers. Kmgl. Vet. A d . , 1892, 79. , 419,217 (1919); 465, 184 (1928). Derivatives of Perthiocyanic and IsoperthiocyanicAcids 49 nism does not explain the formation of compound (111). Supposing the then the structure of thiocyanogen is assumed to be S=C=N-S-C=N, following mt of reactions (23) would take place. Oxidation of this structure (VI) would give compound (111) (24). HC1 (111) chloride which would explain (111) the activation of the halogen attached to the carbon atom.

26,526 (1940); Chem. , 35,3254 (1941). , 24,394 (1891). 18 Chakravarti, J . Chem. , 123,964 (1923). l1 Ishikawa, Chem. , 19, 3087 (1925); Sci. Papers Inst. Phys. Chem. Research 9 (Tokyo), 3, 147 (1925). 3- and 5-Aryl Substituted 1,2,4-"hiidiazoles 53 this conclusion and deduced that the product was 3,5-diphenyl-1,2,4thiadiarole. This compound on reduction gave benzyl benzamidine (11). Ishikawa also prepared this thiadiarole using thiobenmmide and thionyl chloride (12). S c&--(2/ N' N1I H, -C&I, CsHoCSNHt - C&IC=NH (11) AHCH&~HI S ~ 0 ~ 1 SOP % + HCI + CsHs-C A \K ___) (12) 4-J-CJ3, In the reactions which use sulfur chloride and thionyl chloride, a small amount of a red unstable intermediate was formed.

Proof of the structure (XXI) was accomplished as shown in equations (24-33). 2(8CaNdo (XW (CN)cSa (XXI) (CN)& + Hg(CN)r + 2NaOH + (CN)St (XXI) (CN)Sa (XXI) + 4 NaOH + KCN NalNtC sodium cyanamide S - - - Hg(WCaNi)o (XX) + (CN),Sa (=I) (28) NaSsCaNa + NaOCN (291 NarSICIN2 + 2NaOCN (30) (CN)2 cyanogen + NaN(CN)t sodium dicysnamide KSsCsNa + Na8CsNa (31) (32) S The other product from the decomposition of the hexathiocyanate was believed to be either 3-thiocyano-5-mercapto-1,2,Pthiadiazole(XXII) 1‘ Werbiick, Svensk Kern.

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