Catalyst-Free, One-Pot, Expeditious Synthesis of Aminoalkylnaphthols at Room Temperature

REFERENCES

• et al. . Substituted 1 and 2-naphthol Mannich bases. U.S. Patent 7,202,242 B2, 2007.
   Google Scholar
• Lu , J. ; Xu , X. ; Wang , C. ; He , J. ; Hu , Y. ; Hu , H. Synthesis of chiral ligands derived from the Betti base and their use in the enantioselective addition of diethylzinc to aromatic aldehydes . Tetrahedron Lett. 2002 , 43 , 8367 – 8369 .
   Web of Science ®Google Scholar
• Brown , P. D. Matrix metalloproteinase inhibitors in the treatment of cancer . Med. Oncol. 1997 , 14 , 1 – 10 .
   PubMed Web of Science ®Google Scholar
• Johnson , K. W. ; Lofland , D. ; Moser , H. E. PDF inhibitors: An emerging class of antibacterial drugs . Curr. Drug Targets: Infect. Disord. 2005 , 5 , 39 – 52 .
   PubMedGoogle Scholar
• Lowther , W. T. ; Matthews , B. W. Structure and function of the methionine aminopeptidases . Biochim. Biophys. Acta 2000 , 1477 , 157 – 167 .
   PubMed Web of Science ®Google Scholar
• Waller , A. S. ; Clements , J. M. Novel approaches to antimicrobial therapy: Peptide deformylase . Curr. Opin. Drug Discov. Dev. 2002 , 5 , 785 – 792 .
   PubMed Web of Science ®Google Scholar
• Chappell , L. T. Applications of EDTA chelation therapy . Altern. Med. Rev. 1997 , 2 , 426 – 432 .
   Google Scholar
• Ford , M. D. Heavy Metals, , 4th ed. ; McGraw Hill : New York , 1996 .
   Google Scholar
• Cohen , A. ; Hall , R. A. ; Heath-Brown , B. ; Parkes , M. W. ; Rees , A. H. Oxytocic activity of basic (aminomethyl) derivatives of phenols and related compounds . J. Pharmacol. Chemother. 1957 , 12 , 194 – 208 .
   PubMed Web of Science ®Google Scholar
• (a) Smrcina , M. ; Vyskocil , S. ; Maca , B. ; Polasek , M. ; Claxton , T. A. ; Abbott , A. P. ; Kocovsky , P. Selective cross-coupling of β-naphthoal and 2-naphthylamine derivatives: A facile synthesis of 2,2′, 3-trisubstituted and 2,2′,3,3′-tet rasubstituted 1,l′-binaphthyls . J. Org. Chem. 1994 , 59 , 2156 – 2163 ; (b) Smrcina , M. ; Lorenc , M. ; Hanus , V. ; Sedmera , P. ; Kocovsky , P. Synthesis of enantiomerically pure 2,2′-dihydroxy-1,l′-binaphthyl, 2,2′-diamino-l,l′-binaphthyl and 2-amino-2′-hydroxy-l,l′-binaphthyl: Comparison of processes operating as diastereoselective crystallization and as second-order asymmetric transformation . J. Org. Chem. 1992 , 57 , 1917 – 1920 ; (c) Vyskocil , S. ; Jaracz , S. ; Smrcina , M. ; Sticha , M. ; Hanus , V. ; Polasek , M. ; Kocovsky , P. Synthesis of N-alkylated and N-arylated derivatives of 2-amino-2′-hydroxy-1,1′-binaphthyl (NOBIN) and 2,2′-diamino-1,1′-binaphthyl and their application in the enantioselective addition of diethylzinc to aromatic aldehydes . J. Org. Chem. 1998 , 63 , 7727 – 7737 ; (d) Yuan , Y. ; Li , X. ; Sun , I. ; Ding , K. L. To probe the origin of activation effect of carboxylic acid and (+)-NLE in tridentated titanium catalyst systems . J. Am. Chem. Soc. 2002 , 124 , 14866 – 14867 ; (e) Kim , Y. ; Singer , R. A. ; Carreira , E. R. Total synthesis of macrolactin a with versatile catalytic, enantioselective dienolate aldol addition reactions . Angew. Chem. Int. Ed. 1998 , 37 , 1261 – 1263 .
   Web of Science ®Google Scholar
• Cardellicchio , C. ; Ciccarella , G. ; Naso , F. ; Perna , F. ; Tortorella , P. Use of readily available chiral compounds related to the Betti base in the enantioselective addition of diethylzinc to aryl aldehydes . Tetrahedron 1999 , 55 , 14685 – 14692 .
   Web of Science ®Google Scholar
• Cardellicchio , C. ; Ciccarella , G. ; Naso , G.F. ; Schingaro , E. ; Scordari , F. The Betti base: Absolute configuration and routes to a family of related chiral nonracemic bases . Tetrahedron: Asymmetry 1998 , 9 , 3667 – 3675 .
   Web of Science ®Google Scholar
• Palmieri , G. A practical o-hydroxybenzylamines-promoted enantioselective addition of dialkylzincs to aldehydes with asymmetric amplification. Tetrahedron: Asymmetry 2000, 11, 3361–3373
   Web of Science ®Google Scholar
• Liu , D. X. ; Zhang , L. C. ; Wang , Q. ; Da , C. S. ; Xin , Z. Q. ; Wang , R. ; Choi , M. C. K. ; Chan , A. S. C. The application of chiral aminonaphthols in the enantioselective addition of diethylzinc to aryl aldehydes . Org. Lett. 2001 , 3 , 2733 .
   PubMed Web of Science ®Google Scholar
• Cimarelli , C. ; Palmieri , G. ; Volpini , E. A practical stereoselective synthesis of secondary and tertiary aminonaphthols: Chiral ligands for enantioselective catalysts in the addition of diethylzinc to benzaldehyde . Tetrahedron: Asymmetry 2002 , 13 , 2417 – 2426
   Web of Science ®Google Scholar
• Cimarelli , C. ; Mazzanti , A. ; Palmieri , G. ; Volpini , E. Solvent-free asymmetric aminoalkylation of electron-rich aromatic compounds: stereoselective synthesis of aminoalkylnaphthols by crystallization-induced asymmetric transformation . J. Org. Chem. 2001 , 66 , 4759 – 4765 .
   PubMed Web of Science ®Google Scholar
• Ji , J. X. ; Qiu , L. Q. ; Yip , C. W. ; Chan , A. S. C. A convenient, one-step synthesis of optically active tertiary aminonaphthol and its applications in the highly enantioselective alkenylations of aldehydes . J. Org. Chem. 2002 , 68 , 1589 – 1590 .
   Web of Science ®Google Scholar
• Betti , M. Condensation between β-naphthol, aldehydes, and amines . Gazz. Chim. Ital. 1900 , 30 , 310 – 316 .
   Google Scholar
• (a) Katritzky , A. R. ; Abdel-Fattah , A. A. A. ; Tymoshenko , D. O. ; Belyakov , S. A. ; Ghiviriga , I. ; Steel , P. J. Amino(hetero)arylmethylation of phenols with N-[α -amino(hetero)arylmethyl]benzotriazoles . J. Org. Chem. 1999 , 64 , 6071 – 6075 ; (b) Saidi , M. R. ; Azizi , N. ; Naimi-Jamal , M. R. Lithium perchlorate–assisted, one-pot, three-component aminoalkylation of electron-rich aromatic compounds . Tetrahedron Lett. 2001 , 42 , 8111 – 8113 .
   Web of Science ®Google Scholar
• Jha , A. ; Paul , N. K. ; Trikha , S. ; Cameron , T. S. Novel synthesis of 2-naphthol Mannich bases and their NMR behavior . Can. J. Chem. 2006 , 84 , 843 – 853 .
   Web of Science ®Google Scholar
• Kumar , A. ; Gupta , M. K. ; Kumar , M. Non-ionic surfactant–catalyzed synthesis of Betti base in water . Tetrahedron Lett. 2010 , 51 , 1582 – 1584 .
   Web of Science ®Google Scholar
• (a) Cardelliccho , C. ; Capozzi , M. A. M. ; Naso , F. The Betti base: The awakening of a sleeping beauty . Tetrahedron: Asymmetry 2010 , 21 , 507 – 517 ; (b) Betti , M. β-Naphthol phenylaminomethane . Org. Synth. Coll. Vol. 1 , 1941 , 381 ; (c) Ghandi , M. ; Olyaei , A. ; Raoufmoghaddam , S. One-pot, three-component uncatalyzed quantitative synthesis of new aminonaphthols (Betti bases) in water . Synth. Commun. 2008 , 38 , 4125 – 4138 .
   Web of Science ®Google Scholar