By L. L. Bambas, Arnold Weissberger
The Chemistry of Heterocyclic Compounds, because its inception, has been well-known as a cornerstone of heterocyclic chemistry. every one quantity makes an attempt to debate all elements – houses, synthesis, reactions, physiological and commercial importance – of a selected ring approach. to maintain the sequence up to date, supplementary volumes masking the new literature on every one person ring method were released. Many ring platforms (such as pyridines and oxazoles) are handled in designated books, each one including separate volumes or elements facing diversified person themes. With all authors are famous experts, the Chemistry of Heterocyclic Chemistry is taken into account around the world because the imperative 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
Flquinoline Ref. 1 Compound 1317 B e m I l . 2 . 5]bis-1J2J~thiadiole I n k No. ,O 115 226 dec. 224-6 Structure and numbering according to Ring Zndm a - Lcf NH* Methodpf preparation T A B U V. Preparation of 1,2,3-Thiadiazoles in Condensed Systems Other Than Benrothiadiazole Green and Perkin, J . , 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 -~.
If the reaction was not kept cool, then triphenylguanidine w&s obtained. Oxidation of the thiadiaeolidine in alcohol with bromine gave triphenylguanidine. Concentrated hydrochloric acid split 2,4diphenyl-3,5-bis(phenylimino)1,2,4-thiadiazolidine into triphenylguanidine (6). , 36,3121 (1903). , 23, 357 (1890). , 394,284 (1912).
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.