Synthesis of 7-Substituted-(2,3-dihydro-1,4-benzodioxin-5-yl)-piperazine

REFERENCES

• Van Steen , B. J. ; van Wijngaarden , I. ; Ronken , E. ; Soudijn , W. Functional characteristics of a series of N4-substituted 1-(2,3-dihydro-1,4-benzodioxin-5-yl)piperazines as 5-HT1A receptor ligands structure–activity relationships . Biorg. Med Chem Lett. 1998 , 8 , 2457 ; (b) Van Steen, B. J.; van Wijngaarden, I.; Tulp, M. T. M.; Soudijn, W. A series of N4-imidoethyl derivatives of 1-(2,3-dihydro-1,4-benzodioxin-5-yl)piperazine as 5-HT1A receptor ligands: Synthesis and structure–affinity relationships. J. Med. Chem. 1995, 38, 4303; (c) Gaster, L. M.; Blaney, F. E.; Davies, S.; Duckworth, D. M.; Ham, P.; Jenkins, S.; Jennings, A. J.; Joiner, G. F.; King, F. D.; Mulholland, K. R.; Wyman, P. A.; Hagan, J. J.; Hatcher, J.; Jones, B. J.; Middlemiss, D. N.; Price, G. W.; Riley, G.; Roberts, C.; Routledge, C.; Selkirk, J.; Slade, P. D. The selective 5-HT1B receptor inverse agonist 1′-methyl-5-[[2′-methyl-4′-(5-methyl-1,2,4-oxadiazol-3-yl)biphenyl-4-yl]carbonyl]-2,3,6,7-tetrahydro-spiro-[furo[2,3-f]indole-3,4′-piperidine] (SB-224289) potently blocks terminal 5-HT autoreceptor function both in vitro and in vivo. J. Med. Chem. 1998, 41, 1218; (d) Peglion, J.; Goument, B.; Despaux, N.; Charlot, V.; Giraud, H.; Nisole, C.; Newman-Tancredi, A.; Dekeyne, A.; Bertrand, M.; Genissel, P.; Millan, M. Improvement in the selectivity and metabolic stability of the serotonin 5-HT1A ligand, S 15535: A series of cis- and trans-2-(arylcycloalkylamine) 1-indanols J. J. Med. Chem. 2002, 45, 165; (e) Reitz, A. B.; Baxter, E. W.; Codd, E. E.; Davis, C. B.; Jordan, A. D. All orally active benzamide antipsychotic agents with affinity for dopamine D2, serotonin 5-HT1A, and adrenergic α1 receptors. J. Med. Chem. 1998, 41, 1997 .
   Google Scholar
• Orús , L. ; Martínez , J. ; Pérez , S. ; Oficialdegui , A. M. ; Del Castillo , J.-C. ; Mourelle , M. ; Lasheras , B. ; del Río , J. ; Monge , A. New 3-[4-(3-substituted phenyl)piperazin-1-yl]-1-(benzo[b]thiophen-3-yl)propanol derivatives with dual action at 5-HT1A serotonin receptors and serotonin transporter as a new class of antidepressants . Pharmazie 2002 , 57 , 515 ; (b) Mishani, E.; Dence, C. S.; McCarthy, T. J.; Welch, M. J. Formation of phenylpiperazines by a novel alumina supported bis-alkylation. Tetrahedron. Lett., 1996, 37, 319 .
   Google Scholar
• Kwong , F. Y. ; Klapars , A. ; Buchwald , S. L. Copper-catalyzed coupling of alkylamines and aryl iodides: An efficient system even in an air atmosphere . Org. Lett. 2002 , 4 , 581 ; (b) Kerrigan, F.; Martin, C.; Thomas, G. H. Synthesis of arylpiperazines via palladium-catalysed aromatic amination reactions of bromoarenes with N-tert-butoxycarbonylpiperazine. Tetrahedron Lett. 1998, 39, 2219 .
   PubMed Web of Science ®Google Scholar
• Furlano , D. C. ; Kink , K. An improved synthesis of 4-fluoroveratrole. Efficient route to 6-fluoroveratraldehyde and 6-fluoro-D,L-DOPA . J. Org. Chem. 1986 , 51 , 4073 ; (b) Daukshas, V. K.; Martinkus, R. S.; Kuleshyus, V. A. Synthesis of 2,3-dimethoxy-5-fluoro and 4,5-dimethoxy-2-fluoro substituted phenylacetic and phenylacetoxyhydroxamic acids. J. Org. Chem. USSR (Engl. Trans.) 1984, 20, 465 .
   Google Scholar
• Daukshas , V. K. ; Balyavichyus , L. Z. ; Udrenaite , É. B. ; Purvanetskas , G. V. ; Urba , V. A. ; Dembinskene , I. A. ; Gineitite , V. L. ; Rukshenas , A. Y. ; Bal'sis , S. Y. Electrophilic substitution of 5- and 6-substituted benzo-1,4-dioxanes . Chem. Heterocycl. Comp. 1978 , 14 , 1188 ; Khimiya Geterotsiklicheskikh Soedinenii 1978, 11, 1465 .
   Google Scholar
• Zolfigol , M. A. ; Ghaemi , E. ; Madrakian , E. Trichloroisocyanuric acid/NaNO2 as a novel heterogeneous system for the selective mononitration of phenols under mild conditions . Synlett 2003 , 2 , 191 .
   Google Scholar
• Roy , A. ; Reddy , K. R. ; Mohanta , P. K. ; Ila , H. ; Junjappa , H. Hydrogen peroxide/boric acid: An efficient system for oxidation of aromatic aldehydes and ketones to phenols . Synth. Commun. 1999 , 29 , 3781 .
   Web of Science ®Google Scholar
• Backstrom , R. ; Honkanen , E. ; Pippuri , A. ; Kairisalo , P. ; Pystynen , J. ; Heinola , K. ; Nissinen , E. ; Linden , I. B. ; Mannisto , P. T. ; Kaallola , S. ; Pohto , P. Synthesis of some novel potent and selective catechol O-methyltransferase inhibitors . J. Med. Chem. 1989 , 32 ( 4 ), 841 .
   PubMed Web of Science ®Google Scholar
• Bandgar , B. P. ; Makone , S.S. Organic reactions in water: Highly rapid CAN mediated one-pot synthesis of nitriles from aldehydes under mild conditions . Synlett 2003 , 2 , 262 .
   Google Scholar