Reaction path of aqueous sodium hydroxide induced ring opening of 4-bromo-3,4-diphenyl-2-isoxazolin-2-one

1984 ◽  
Vol 49 (11) ◽  
pp. 2071-2073 ◽  
Author(s):  
Egle M. Beccalli ◽  
Alessandro Marchesini ◽  
Francesco Sannicolo
Keyword(s):  
Sodium Hydroxide ◽  
Ring Opening ◽  
Reaction Path ◽  
Aqueous Sodium Hydroxide ◽  
Aqueous Sodium

Base-catalysed ring opening of N-(aminothioxomethyl)-5,6-dihydro-2-methyl-1,4-oxathiin-3-carboxamides

1980 ◽  
Vol 58 (19) ◽  
pp. 2044-2048 ◽  
Author(s):  
Marshall Kulka
Keyword(s):  
Sodium Hydroxide ◽  
Ring Opening ◽  
Room Temperature ◽  
Aqueous Sodium Hydroxide ◽  
Rearrangement Product ◽  
Aqueous Sodium

The condensation of 5,6-dihydro-2-methyl-1,4-oxathiin-3-carbonyl isothiocyanate (1) with ethyl 3-phenylamino-2-butenoate (2) has yielded a mixture of ethyl 1,4-dihydro-2-(5,6-dihydro-2-methyl-1, 4-oxathiin-3-yl)-6-methyl-1-phenyl-4-thioxo-5-pyrimidine carboxylate (3) and N-[(phenylamino)thioxomethyl]-5,6-dihydro-2-methyl-1,4-oxathiin-3-carboxamide (4, R′ = phenyl). It has been discovered that compounds 4, in general, rearrange to 1-substituted-2,3-dihydro-5-[(2-hydroxyethyl)thio]-6-methyl-2-thioxo-4(1H)-pyrimidinones (5) at room temperature when stirred with dilute aqueous sodium hydroxide. The products of the reaction of 5,6-dihydro-2-methyl-1,4-oxathiin-3-carbonyl isothiocyanate (1) and phenylhydrazine, when treated with dilute aqueous sodium hydroxide, did not yield the rearrangement product 5 (R′ = NHC6H5). Instead, a mixture of the two triazole-3-thiones 9 and 10 was formed. N,2-Bis(5,6-dihydro-2-methyl-1,4-oxathiin-3-carbonyl)hydrazinecarbothioamide (12) with dilute aqueous sodium hydroxide yielded one rearrangement product (out of a possible four), namely, 5-6-dihydro-2-methyl-N-[1,2,3,4-tetrahydro-5-[(2-hydroxyethyl)thio]-6-methyl-4-oxo-2-thioxo-1-pyrimidinyl]-1,4-oxathiin-3-carboxamide (13).

scholarly journals Triple Helix of Scleroglucan in Dilute Aqueous Sodium Hydroxide

1981 ◽  
Vol 13 (12) ◽  
pp. 1135-1143 ◽  
Author(s):  
Toshio Yanaki ◽  
Takemasa Kojima ◽  
Takashi Norisuye
Keyword(s):  
Sodium Hydroxide ◽  
Triple Helix ◽  
Aqueous Sodium Hydroxide ◽  
Aqueous Sodium
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