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XVI Table of Contents
17.1.3 Product Subclass 3: One Sulfur, Selenium, or Tellurium Atom
and One Nitrogen or Phosphorus Atom
H. Ulrich
17.1.3 Product Subclass 3: One Sulfur, Selenium, or Tellurium Atom
and One Nitrogen or Phosphorus Atom .................................. 117
17.1.3.1 1,4-Thiazines ............................................................. 117
17.1.3.1.1 Synthesis by Ring-Closure Reactions ....................................... 118
17.1.3.1.1.1 By Formation of Two S—C Bonds and One N—C Bond ....................... 118
17.1.3.1.1.1.1 Method 1: From Ketones, Aziridine, and Sulfur ........................ 118
17.1.3.1.1.1.2 Method 2: From b-Aminoacrylates and Sulfur Dichloride
or Sulfur Monochloride .................................... 118
17.1.3.1.1.2 By Formation of One S—C and One N—C Bond .............................. 119
17.1.3.1.1.2.1 Method 1: From 2-Sulfanylacetamides and 2-Halocarbonyl Compounds 119
17.1.3.1.1.2.2 Method 2: From 2-Aminoethanethiols ................................ 120
17.1.3.1.1.2.3 Method 3: From 1-Aza-4-thiabutadienes and Alkynes or Alkenes ....... 120
17.1.3.1.1.2.4 Method 4: From a-Sulfanyl Ketones and Aziridine ..................... 121
17.1.3.1.1.3 By Formation of Two N—C Bonds .......................................... 122
17.1.3.1.1.3.1 Method 1: From Bis(2-oxoalkyl) Sulfides .............................. 122
17.1.3.1.1.4 By Formation of One S—C and One C—C Bond .............................. 122
17.1.3.1.1.4.1 Method 1: From Alkyl [(3-Phenyl-2-propynoyl)anilino]acetates and
Aryl Isothiocyanates ....................................... 122
17.1.3.1.1.5 By Formation of Two C—C Bonds .......................................... 123
17.1.3.1.1.5.1 Method 1: From Cyanodithioimidocarbonates and Dimethyloxosulfonium
Methylide ................................................ 123
17.1.3.1.1.6 By Formation of One N—C Bond ........................................... 123
17.1.3.1.1.6.1 Method 1: From (Acetonylsulfanyl)acetamides ........................ 123
17.1.3.1.2 Synthesis by Ring Transformation .......................................... 124
17.1.3.1.2.1 By Ring Enlargement ..................................................... 124
17.1.3.1.2.1.1 Method 1: From 1,3-Thiazoles ........................................ 124
17.1.3.1.2.1.2 Method 2: From 2-Oxazolidinones and Thioglycolates ................. 124
17.1.3.1.2.2 Formal Exchange of Ring Members with Retention of the Ring Size .......... 125
17.1.3.1.2.2.1 Method 1: From 1,4-Oxathiin-3-carboxamides ......................... 125
17.1.3.1.2.2.2 Method 2: From 2,5-Diphenyl-1,4-dithiin 1,1,4,4-Tetroxide
and Sodium Azide ......................................... 125
17.1.3.1.3 Aromatization ............................................................ 125
17.1.3.1.3.1 Method 1: By Deprotonation and S-Alkylation of 2H-1,4-Thiazines ...... 125
17.1.3.1.4 Synthesis by Substituent Modification ..................................... 126
17.1.3.1.4.1 Method 1: By Deamination of 3,4-Dihydro-2H-1,4-thiazin-4-amines .... 126
17.1.3.1.4.2 Method 2: By Dealkoxylation of Pyrrolothiazines ...................... 126