By L. L. Bambas, Arnold Weissberger
The Chemistry of Heterocyclic Compounds, considering the fact that its inception, has been famous as a cornerstone of heterocyclic chemistry. every one quantity makes an attempt to debate all points – homes, synthesis, reactions, physiological and commercial value – of a particular ring process. to maintain the sequence updated, supplementary volumes masking the hot literature on every one person ring procedure were released. Many ring structures (such as pyridines and oxazoles) are taken care of in precise books, every one together with separate volumes or components facing diverse person issues. With all authors are famous specialists, the Chemistry of Heterocyclic Chemistry is taken into account around the globe because the critical source for natural, bioorganic, and medicinal chemists.
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Additional info 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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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.
83, 1201 (1903). , 277,221 (1893). Bamberpr, Bocking, and Kraus, J . prakl. , 105, 251 (1923). 6 Bamberacr. Baum. ,lOS, , J . vrakl. 266 (1923). ,454, 172 (1927). , 527,38(1937). 1]-1,2,3-thiadiamzole -~. TABLE V (Continued) C' 0 HNO? 5 89 w iF I& Chemistry of Heterocyclic Compounds, Volume4 L. L. Bambas Copyright 0 1952 by Interscience Publishers, Inc. Derivatives of the 1,2,4=Thiadiazoles and Their Selenium Analogs 1,2,4-Thiadiazoles ,S (Ring I d e x No. 71) I. Derivatives of Perthiocyanic and Isoperthiocyanic Acids There is considerable literature on variously substituted perthiocyanic acid derivatives having structures designated as 1,2,bthiadiazoles.
3,346 (1870). * KIsaon, J . pmkt. , (2138,366 (1888). 35 38 Thictditwoles cyanic acid (which could be changed to isoperthiocyanic acid) was as given in equation (2). He postulated that the transformation took part in two steps (3). The preparation of the “labile or real” perthiocyanic acid consisted of digesting isoperthiocyanic acid with barium hydroxide. Sulfur at first precipitated and then largely redissolved. A barium salt of perthiocyanic acid was isolated. This salt in a dilute solution when precipitated with hydrochloric acid gave isoperthiocyanic acid.