Title of article :
A novel alkylation procedure using MW irradiation for the synthesis of 1,2,3-trisubstituted 1,4,5,6,7,8-hexahydro-1,3-diazocinium salts from their corresponding 1,2-diaryldiazocines
Author/Authors :
Ramيrez، نويسنده , , Marيa A. and Ortiz، نويسنده , , Gisela M. and Salerno، نويسنده , , Alejandra and Perillo، نويسنده , , Isabel A. and Blanco، نويسنده , , Marيa M.، نويسنده ,
Issue Information :
هفته نامه با شماره پیاپی سال 2012
Pages :
3
From page :
1367
To page :
1369
Abstract :
In this work, we describe the synthesis of a series of 1,2,3-trisubstituted-1,4,5,6,7,8-hexahydro-1,3-diazocinium salts (1) by alkylation of the corresponding 1,2-diaryl-1,4,5,6,7,8-hexahydro-1,3-diazocines (2). Compounds 2 were obtained by ethyl polyphosphate-promoted cyclocondensation of N-aroyl-N′-arylpentamethylenediamines (3). Reaction of compounds 2 with alkyl iodides led to 1,2,3-trisubstituted 1,4,5,6,7,8-hexahydro-1,3-diazocinium iodides (1), a new family of cyclic amidinium salts. The best yields for the alkylation were achieved using a mixture of DCM–DMSO (10:1) as solvent. The reaction times of both, the cyclocondensation of compounds 3 and the reaction of 2 with alkyl halides, are dramatically decreased when using microwave irradiation.
Keywords :
Cyclic amidinium salts , Ethyl polyphosphate , Microwaves , N-Alkylation , Cyclic amidines
Journal title :
Tetrahedron Letters
Serial Year :
2012
Journal title :
Tetrahedron Letters
Record number :
1880263
Link To Document :
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