Synthesis of 1,4-diaryl-piperazine-2,5-diones: New behavior of N,N-dimethylformamide dimethyl acetal (DMFDMA)

Synthetic Communications

Volumn 38, Issue 3, 2008, Pages 376-382

  Abu Shanab, Fathi A ^a   Al Harrasi, Ahmed ^b   Mousa, Sayed A S ^a  

^a Assiut Branch   (Egypt)

^b SULTAN QABOOS UNIVERSITY   (Oman)

Author keywords

chloroacetamides 1,4 diarylpiperazine 2,5 diones; Condensation; Dimerization; N,N dimethylformamide dimethyl acetal

Indexed keywords

1,4 DIARYL PIPERAZINE 2,5 DIONE DERIVATIVE; 1,5 DIARYL 3,7 DIMETHOXY 1H,5H [1,5]DIAZOCINE 2,6 DIONE DERIVATIVE; ACETAL DERIVATIVE; CHLOROACETAMIDE; N,N DIMETHYLFORMAMIDE DIMETHYL ACETAL; PIPERAZINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; SYNTHESIS;

EID: 38649134819     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910701767098     Document Type: Article

References (13)

1. Granik, V. G.; Zhidkova, A. M.; Glushkov, R. G. Advances in the chemistry of the acetals of acid amides and lactams. Russ. Chem. Rev. 1977, 46, 361.
2. Abdulla, R. F.; Brinkmeyer, R. S. The chemistry of formamide acetals. Tetrahedron 1979, 35, 1675.
3. An-Lli, P. L.; Brocchetta, M.; Palano, D.; Visigalli, M. Mild conversion of primary carboxamides into carboxylic esters. Tetrahedron Lett. 1997, 38 (13), 2367.
4. Abu-Shanab, F. A.; Redhouse, A. D.; Thompson, J. R.; Wakefield, B. J. Synthesis of 2,3,5,6-tetrasubstituted pyridines from enamines derived from N,N-dimethylformamide dimethyl acetal. Synthesis 1995, 557.
5. Abu-Shanab, F. A.; Aly, F. M.; Wakefield, B. J. Synthesis of substituted nicotinamides from enamines derived from N,N-dimethylformamide dimethyl acetal. Synthesis 1995, 923.
6. Abu-Shanab, F. A. Synthesis of 2,3,4,6-tetrasubstituted pyridines as precursors to bicycles and polycycles. J. Chem. Res., Synop. 1999, 430.
7. Abu-Shanab, F. A.; Elkholy, Y. M.; Elnagdi, M. H. Enaminones as building blocks in organic synthesis: synthesis of new polyfunctional pyridines, condensed pyridines and pentasubstituted benzene. Synth. Commun. 2002, 32, 3493.
8. Castro, S.; Chicharro, R.; Aran, V. J. Synthesis of quinoxaline derivatives from substituted acetanilides through intramolecular quaternization reactions. J. Chem. Soc., Perkin Trans. 1, 2002, 790.
9. 3-tetrapeptide scaffolds. Tetrahedron 2001, 56, 7947.
10. Ruiz, J. R.; Aran, V. J.; Asensio, J. L.; Flores, M.; Stud, M. Synthesis of quaternary indoxyl derivatives by intramolecular cyclization of some substituted acetophenones. Liebigs Ann. Chem. 1994, 679.
11. Okawara, T.; Noguchi, Y.; Matsuda, T.; Furukawa, M. Convenient syntheses of piperazine-2,5-diones and lactams from halocarboxamides using phase transfer catalysts. Chem. Lett. 1981, 185.
12. Cavicchioni, G.; Scrimin, P.; Veronese, A. C.; Balboni, G.; D'Angeli, F. Base-promoted reactions of α-halogeno-alkylanilides. J. Chem. Soc. Perkin Trans. 1, 1982, 2969.
13. Abenius, P. W. Ueber einige aromatische halogensubstituirte Acetamidoderivate und daraus erhaltene Verbindungen. Chem. Ber. 1888, 21, 1665.