Some ring a methoxy-derivatives of estrone and estradiol-17β

Conrow, R. B.; Cantrall, Edward W.; Bernstein, Seymour

doi:10.1016/0039-128x(67)90115-8

Cited by 3 publications

(1 citation statement)

References 10 publications

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“…Rearrangement of the dibenzofuran derivative (lq) proceeded extremely slowly and in poor (21%) yield. This may be attributed to steric strain in the Meisenheimer intermediate (4) and molecular modelling Me calculations tend to support this explanation; from an AMPAC computation the heat of formation of (4) was higher (3.7 kJ mol-') than that of the corresponding structure without the carbon-carbon aryl bond.…”

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confidence: 95%

The conversion of phenols to primary and secondary aromatic amines via a Smiles rearrangement

Coutts¹,

Southcott²

1990

J. Chem. Soc., Perkin Trans. 1

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The conversion of phenols to 2-aryloxy-2-methylpropanamides (1 ) and the Smiles rearrangement of these to N-aryl-2-hydroxy-2-methyl propanamides are described; hydrolysis of the latter compounds yields anilines. The scope and limitations of reaction are discussed. Routes, some involving alactams, from phenols t o N-substituted derivatives of (1) have been developed. Under the conditions of the Smiles rearrangement these secondary 2-methylpropanamides can form directly anilides, N-al kylani I ines, or benzoxazinones.There are few general methods for the direct conversion of phenols to anilines. Transformations involving 4-chloro-2phenylquinazoline are limited to substrates resistant to high temperatures and basic conditions, while a more versatile route via diethyl phosphate esters of phenols requires the use of toxic diethyl chlorophosphate and of potassium in liquid ammonia. The well known Bucherer reaction is restricted to naphthalenes and related heterocycles.that 2-aryloxy-2-methylpropanamides (l), on treatment with base, undergo a Smiles rearrangement to give N-aryl-2-hydroxy-2-methylpropanamides (2) which, after acid or base hydrolysis yield anilines (Scheme 1). For ethers (1) in which the aryl moiety contains It has, however, been reported ArOC(Me,)CONH, --+ ArNHCOC(Me,)OH -ArNH, Scheme 1.

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confidence: 95%