LEADER 04959nam 2200649 a 450 001 9910143643403321 005 20170809170608.0 010 $a1-280-54200-4 010 $a9786610542000 010 $a0-471-65699-2 010 $a0-471-65691-7 035 $a(CKB)111090529064314 035 $a(EBL)183816 035 $a(OCoLC)808021508 035 $a(SSID)ssj0000120566 035 $a(PQKBManifestationID)11146493 035 $a(PQKBTitleCode)TC0000120566 035 $a(PQKBWorkID)10081055 035 $a(PQKB)10996486 035 $a(MiAaPQ)EBC183816 035 $a(EXLCZ)99111090529064314 100 $a20040610d2004 uy 0 101 0 $aeng 135 $aur|n|---||||| 181 $ctxt 182 $cc 183 $acr 200 14$aThe chemistry of 1,2,3-Thiadiazoles$b[electronic resource] /$fVasiliy A. Bakulev, Wim Dehaen 210 $aHoboken, N.J. $cJohn Wiley & Sons$dc2004 215 $a1 online resource (261 p.) 225 1 $aThe chemistry of heterocyclic compounds ;$vv. 62 300 $aDescription based upon print version of record. 311 $a0-471-32662-3 320 $aIncludes bibliographical references and index. 327 $aTHE CHEMISTRY OF 1,2,3-THIADIAZOLES; The Chemistry of Heterocyclic Compounds Introduction to the Series; Preface; Acknowledgments; Contents; 1 Synthesis of 1,2,3-thiadiazoles; 1.1 Cyclization of Hydrazones with Thionyl Chloride (Hurd-Mori Synthesis); 1.1.1 Scope and Limitations; 1.1.2 Mechanism of the Hurd-Mori Reaction; 1.1.3 Application of the Hurd-Mori Reaction in Organic Synthesis; 1.2 Cycloaddition of Diazoalkanes onto a C=S bond (Pechmann Synthesis); 1.3 Heterocyclization of ?-diazo Thiocarbonyl Compounds (Wolff Synthesis) 327 $a1.3.1 Introduction of a Diazo Function into Compounds Containing a C=S Bond1.3.2 Introduction of a C=S Bond in the ?-position to a Diazo Group; 1.3.3 Simultaneous Introduction of Diazo and Thiocarbonyl Functions; 1.4 Transformations of other Sulfur-containing Heterocyclic Compounds; 1.5 Elaboration of Preformed 1,2,3-Thiadiazoles; 1.5.1 Carboxylic Acids; 1.5.2 Functional Derivatives of Carboxylic Acids; 1.5.3 Aldehydes; 1.5.4 Amino-1,2,3-Thiadiazoles; 1.5.5 Halo Derivatives; 1.5.6 5-Hydrazino-, 5-Mercapto-1,2,3-Thiadiazoles and 5-Sulfide Derivatives 327 $a1.5.7 2-(1,2,3-Thiadiazol-5-yl)acetic Acid Derivatives1.5.8 Alkenyl-1,2,3-Thiadiazoles; 1.5.9 5-Hydroxyiminomethyl- and 5-Diazomethyl-1,2,3-Thiadiazoles; 1.5.10 4-Hydroxymethyl-1,2,3-Thiadiazoles; 1.6 Tables; 1.7 Selected Procedures; 1.7.1 1,2,3-Thiadiazole-4-Carbaldehyde; 1.7.2 4-Phenyl-1,2,3-Thiadiazole; 1.7.3 4-Phenyl-1,2,3-Thiadiazole-5-Carbaldehyde; 1.7.4 4-Phenyl-5-Oxyiminomethyl-1,2,3-Thiadiazole; 1.7.5 5-Phenyl-1,2,3-Thiadiazole-4-Carbaldehyde; 1.7.6 5-Chloro-1,2,3-Thiadiazole-4-Carbaldehyde; 1.7.7 Ethyl 5-amino-1,2,3-Thiadiazole-4-Carboxylate; 1.7.7.1 Pechmann Method 327 $a1.7.7.2 Wolff Method1.7.8 Ethyl 5-chloro-1,2,3-Thiadiazole-4-Carboxylate; 1.7.9 4-Phenyl-2-(2,4,6-Trichlorophenyl)-1,2,3-Thiadiazolium Chloride; 1.7.10 5-Amino-4-ethoxycarbonyl-2-phenyl-1,2,3-thiadiazolium bromide; References; 2 Structure of 1,2,3-Thiadiazoles; 2.1 Theoretical Methods; 2.2 Experimental Structural Methods; 2.2.1 X-ray Analysis; 2.2.2 Nuclear Magnetic Resonance Spectroscopy; 2.2.2.1 Proton NMR Spectroscopy; 2.2.2.2 Carbon-13 NMR Spectroscopy; 2.2.2.3 Nitrogen-14 NMR Spectroscopy; 2.2.2.4 Nitrogen-15 NMR Spectroscopy; 2.2.3 Mass Spectrometry; 2.2.4 Other Spectroscopic Data 327 $aReferences3 Chemical Properties of 1,2,3-Thiadiazoles; 3.1 Reactions due to the Reactivity of Ring Atoms; 3.1.1 Reactions with Electrophiles; 3.1.1.1 Protonation; 3.1.1.2 Complexation; 3.1.1.3 Alkylation; 3.1.1.4 Acylation; 3.1.1.5 Oxidation; 3.1.1.6 Electrophilic Substitution of Hydrogen; 3.1.2 Reactions with Nucleophiles; 3.1.2.1 Attack at the Sulfur Atom; 3.1.2.2 Attack at the C(5) Atom; 3.1.2.3 Attacks at H(4) and H(5); 3.1.2.4 Cycloaddition Reactions; 3.2 Reactions of Substituents; 3.2.1 5-Alkyl-1,2,3-thiadiazoles; 3.2.2 1,2,3-Thiadiazole-4-carbaldehyde 327 $a3.2.3 5-Amino-1,2,3-thiadiazole-4-carbothioamide 330 $a1,2,3-Thiadiazoles are a group of heterocycles whose derivatives are important in industry, medicine, and agriculture. This volume provides a complete treatment of this group of heterocycles with an emphasis on syntheses, structural data, properties, reactions, and applications. 410 0$aChemistry of heterocyclic compounds ;$vv. 62. 606 $aThiadiazoles 608 $aElectronic books. 615 0$aThiadiazoles. 676 $a547.59 676 $a547.594 676 $a547/.59/05 700 $aBakulev$b Vasiliy A$0924247 701 $aDehaen$b W$g(Wim)$0924248 801 0$bMiAaPQ 801 1$bMiAaPQ 801 2$bMiAaPQ 906 $aBOOK 912 $a9910143643403321 996 $aThe chemistry of 1,2,3-Thiadiazoles$92074107 997 $aUNINA