Five-membered rings. I. The reaction of 2-methyl-2-oxazoline with phthalimidoacetyl chloride

Hasan, S. K.; Wasson, F. I.; Wolfe, Saul

doi:10.1139/v67-321

Can. J. Chem.

1967

DOI: 10.1139/v67-321

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Five-membered rings. I. The reaction of 2-methyl-2-oxazoline with phthalimidoacetyl chloride

S. K. Hasan¹,

F. I. Wasson²,

Saul Wolfe³

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1968

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Cited by 8 publications

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“…The first stage of these reactions is of interest as a convenient synthetic route to phthalamic acid derivatives (3). The second has been the subject of numerous kinetic investigations (4) because of its relationship to mechanisms of intramolecular 'Part I is S. K. Hasan et al (41).…”

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Five-membered rings. II. Inter and intramolecular reactions of simple amines with N-substituted phthalimides. Methylamine as a reagent for removal of a phthaloyl group from nitrogen

Wolfe¹,

Hasan²

1970

Can. J. Chem.

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A reexamination of the literature on inter and intramolecular reactions of amines with N-substituted phthalimides has led to the demonstration that methylamine is a convenient reagent for removal of a phthaloyl protecting group from nitrogen at room temperature. Application of this procedure (first described in 1896) to the Gabriel synthesis of primary amines and to peptide synthesis is recommended. The simplicity of the reaction is a consequence of the consecutive occurrence of two unexpectedly rapid processes: (1) methylaminolysis of one of the imide bonds; (2) intramolecular catalysis, by an N-methylamido group, of the hydrolysis or aminolysis of an adjacent phthalamido linkage.Some unsuccessful attempts to prepare 2-aminoethylphthalimide are also described.

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Five-membered rings. II. Inter and intramolecular reactions of simple amines with N-substituted phthalimides. Methylamine as a reagent for removal of a phthaloyl group from nitrogen

Wolfe¹,

Hasan²

1970

Can. J. Chem.

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Synthese neuartiger β‐Lactame; 8–Oxo‐5–oxa‐1‐aza‐bicyclo‐[4,2,0]‐octane

Paul

Polczynski

Hilgetag

1968

Zeitschrift fuer Chemie

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β-Lactams: retrospect and prospect

Mukerjee

Singh²

1978

Tetrahedron

146

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Five-membered rings. I. The reaction of 2-methyl-2-oxazoline with phthalimidoacetyl chloride

Cited by 8 publications

References 0 publications

Five-membered rings. II. Inter and intramolecular reactions of simple amines with N-substituted phthalimides. Methylamine as a reagent for removal of a phthaloyl group from nitrogen

Five-membered rings. II. Inter and intramolecular reactions of simple amines with N-substituted phthalimides. Methylamine as a reagent for removal of a phthaloyl group from nitrogen

Synthese neuartiger β‐Lactame; 8–Oxo‐5–oxa‐1‐aza‐bicyclo‐[4,2,0]‐octane

β-Lactams: retrospect and prospect

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