Tetrahedron letters

A synthesis of succinimides and glutarimides from cyclic anhydrides

T Kometani, T Fitz, DS Watt

Index: Kometani, Tadashi; Fitz, Tony; Watt, David S. Tetrahedron Letters, 1986 , vol. 27, # 8 p. 919 - 922

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Citation Number: 24

Abstract

Abstract The transformation of cyclic anhydrides to their corresponding imides involves a mild three-step sequence:(1) reaction with a primary amine,(2) conversion of the intermediate monoamide to an N-hydroxysuccinimidyl ester using N, N′-disuccinimidyl oxalate (DSO), and (3) cyclization by heating the NHS ester in trichloroethylene in the presence of 4-(dimethylamino) pyridine.

The Reaction of Succinic and Glutaric Acid with Amines

[Hoey; Lester Journal of the American Chemical Society, 1951 , vol. 73, p. 4473]

N-Cyanoimides: Reactivity studies with amine nucleophiles

[Stephens, Randall W.; Domeier, Linda A.; Todd, Michael G.; Nelson, Veronica A. Tetrahedron Letters, 1992 , vol. 33, # 6 p. 733 - 736]

Solvent-mediated one-pot synthesis of cyclic N-substituted i...

[Patil, Sambhaji V.; Mahale, Keshao A.; Gosavi, Kirankumar S.; Deshmukh, Ganesh B.; Patil, Nilesh S. Organic Preparations and Procedures International, 2013 , vol. 45, # 4 p. 314 - 320]

N-Cyanoimides: Reactivity studies with amine nucleophiles

[Stephens, Randall W.; Domeier, Linda A.; Todd, Michael G.; Nelson, Veronica A. Tetrahedron Letters, 1992 , vol. 33, # 6 p. 733 - 736]