2832-98-6Relevant articles and documents
One-pot three-component heteroannulation of β-oxo dithioesters, amines and hydroxylamine: Regioselective, facile and straightforward entry to 5-substituted 3-aminoisoxazoles
Samai, Subhasis,Chanda, Tanmoy,Ila, Hiriyakkanavar,Singh, Maya Shankar
supporting information, p. 4026 - 4031 (2013/07/19)
An efficient and highly regioselective one-pot three-component synthesis of previously inaccessible and synthetically demanding 3-(cycloalkyl/alkyl/ arylamino)-5-aryl/alkylisoxazoles has been achieved by the cyclocondensation of β-oxo dithioesters, amines and hydroxylamine in ethanol at reflux. This transformation proceeds via an in situ generated β-oxothioamide by the reaction of the β-oxo dithioester and amine, which undergoes nucleophilic attack by hydroxylamine followed by intramolecular cyclization with the oxo functionality and subsequent dehydration to give 5-substituted 3-aminoisoxazoles as a single regioisomer in good yields. Furthermore, the mechanism of the reaction has been established experimentally and shown to be in agreement with the hard and soft (Lewis) acid and base (HSAB) theory. A highly regioselective synthesis of 5-substituted 3-aminoisoxazoles has been achieved by a one-pot three-component coupling of β-oxo dithioesters, amines and hydroxylamine in ethanol at reflux via an in situ generated β-oxo thioamide intermediate. The mechanism of the reaction has been established experimentally and shown to be in agreement with the HSAB theory. Copyright
Cyclization Reactions of 2-Acyl-1-chloro-enamines with Thioamide Functional Compounds: Alternative Access to the 1,3-Thiazine and 1,3-Oxazine Series
Spitzner, Roland,Freitag, Sabine,Schroth, Werner
, p. 1383 - 1394 (2007/10/02)
2-Acyl-1-chloro-enamines 2 react with thioureas to 2,6-diamino-1,3-thiazinium salts 3, following to usual transformation mode of 1-heterosubstituted acylvinylchlorides A.On the other hand the reaction of 2 with thiobenzamide preferably leads to 4-amino-1,
Ein Zugang zu 2-Acyl-1-chloroenaminen aus Acylketen-dichloriden und sekundaeren Aminen
Schroth, Werner,Spitzner, Roland,Hugo, Sepp
, p. 199 - 203 (2007/10/02)
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