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The reactions of heterocyclic isothiocyanates bearing an ortho ester group with N ‐nucleophiles. The scope and some limitations of the reaction
Author(s) -
Urleb Uroš
Publication year - 1995
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570320112
Subject(s) - chemistry , thiourea , bifunctional , nucleophile , reagent , cysteamine , steric effects , ring (chemistry) , medicinal chemistry , group (periodic table) , primary (astronomy) , organic chemistry , stereochemistry , catalysis , physics , astronomy
Heterocyclic isothiocyanates bearing an o ‐ester group were converted into thiourea derivatives 2, 5, 6, 7 , and 9 using sterically large primary amines or aminoacids, and to the fused ring systems, e.g. 12 H ‐pyrido[3′,2′:4,5]pyrimido[2,1‐ b ]benzothiazol‐12‐one ( 3 ), and 6,7‐dihydro‐9 H ‐thiazolo[3,2‐ a ]thieno[3,2‐ d ]‐pyrimidin‐9‐one ( 13 ), respectively, using bifunctional reagents such as 2‐aminothiophenol or cysteamine.