Efficient synthesis of N-arylpiperazinones via a selective intramolecular Mitsunobu cyclodehydration

Tetrahedron Letters

Volumn 39, Issue 41, 1998, Pages 7459-7462

  Weissman, Steven A ^a   Lewis, Stephanie ^a   Askin, David ^a   Volante, R P ^a   Reider, Paul J ^a  

^a MERCK RESEARCH LABORATORIES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2 METHYLAMINOETHANOL; ANILINE DERIVATIVE; AZIRIDINE; CHLOROACETAMIDE; ETHANOLAMINE; PIPERAZINE DERIVATIVE; PIPERAZINONE DERIVATIVE; UNCLASSIFIED DRUG;

ACYLATION; AMINATION; ARTICLE; CYCLIZATION; DEHYDRATION; DRUG SYNTHESIS;

EID: 0032497606     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01670-0     Document Type: Article

References (24)

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21. 9. Isolated yields of 1a-k generally ranged from 54-94% and are unoptimized.
22. 10. In one example (entry 1c), it was advantageous to pre-form the Mitsunobu complex at 0 °C (15 min age) and then add it to a slurry of the amidoalcohol in EtOAc.
23. 11. We have been unable thus far to observe or isolate any aziridine intermediates in the cyclodehydration step.
24. c 170.9, 140.2, 130.6, 125.8, 121.5, 121.38, 117.9, 60.3, 52.7, 51.5.