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Untersuchungen an 1,3‐Thiazinen, 43. Newman‐Kwart‐Umlagerung bei Thiocarbazoylierungen von Tetrahydro‐2 H ‐1,3‐thiazin‐2‐on und Thiazolidin‐2‐on
Author(s) -
Hanefeld Wolfgang,
Von Gösseln Hans Joachim
Publication year - 1991
Publication title -
liebigs annalen der chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0170-2041
DOI - 10.1002/jlac.199119910175
Subject(s) - chemistry , medicinal chemistry , product (mathematics) , stereochemistry , mathematics , geometry
Investigations on 1,3‐Thiazines, 43. – Newman‐Kwart Rearrangement in the Course of Thiocarbazoylation of Tetrahydro‐2 H ‐1,3‐thiazin‐2‐one and Thiazolidin‐2‐one Thiocarbazoylation of tetrahydro‐2 H ‐1,3‐thiazin‐2‐one ( 1 ) with thiocarbazic acid chlorides leads to N ‐thiocarbazoyl derivatives 5 and N ‐carbazoyl‐tetrahydro‐2 H ‐1,3‐thiazin‐2‐thiones 8 , which are interpreted as products of an O ‐thiocarbazoylation to 6 , subsequent Newman‐Kwart rearrangement to 7 and final S→N transcarbazoylation. Thiocarbazoylation of thiazolidin‐2‐one ( 9 ) yields an isolable Newman‐Kwart rearrangement product 12 and its product 13 of S→N transcarbazoylation.