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Synlett 2010(14): 2109-2113  
DOI: 10.1055/s-0030-1258536
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

tert-Amino Effect in peri-Substituted Naphthalenes: Syntheses of Naphthazepine and Naphthazonine Ring Systems

Ágota Anna Földia, Krisztina Ludányib, Attila Csaba Bényeic, Péter Mátyus*a
a Department of Organic Chemistry, Semmelweis University, Hőgyes Endre utca 7., 1092 Budapest, Hungary
Fax: +36(1)2170851; e-Mail: peter.matyus@szerves.sote.hu;
b Department of Pharmacy, Semmelweis University, Hőgyes Endre utca 7., 1092 Budapest, Hungary
c Department of Chemistry, Laboratory for X-ray Diffraction, University of Debrecen, Egyetem tér 1., 4010 Debrecen, Hungary
Further Information

Publication History

Received 20 May 2010
Publication Date:
30 July 2010 (online)

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Abstract

Novel straightforward syntheses of naphtho-fused azepines and benzazonine via tert-amino effect are described. Starting from 1-naphthylamine, 8-N,N-dialkylaminonaphthalene-1-carb­aldehydes could be obtained in two steps. The aldehyde was prepared by a Suzuki reaction of 8-bromonaphthalene-1-carbaldehyde with ortho-pyrrolidinophenylboronic acid. Treatment of aldehydes with active methylene compounds afforded naphthazepines and novel benzazonine ring system, respectively, through rearrangement of isolable vinyl intermediates or benzo[de]quinolinium derivatives or without isolation of any intermediates. A mechanistic investigation supports an intramolecular hydride transfer for the ring closure to azepine or azonine. Our results indicate that the tert-amino effect may provide a valuable approach to the synthesis of ortho- and peri-fused aza-ring systems.

Key words

tert-amino effect - naphthazepine - naphthazonine - benzo[d,e]quinolinium - peri-interaction

    References and Notes

  • 1 Meth-Cohn O. Suschitzky H. Adv. Heterocycl. Chem.  1972,  14:  211 
    Search in Google Scholar
  • 2a Meth-Cohn O. Adv. Heterocycl. Chem.  1996,  65:  1 
    Search in Google Scholar
  • 2b Quintela JM. Recent Res. Dev. Org. Chem.  2003,  7:  259 
    Search in Google Scholar
  • 2c Mátyus P. Éliás O. Tapolcsányi P. Polonka-Bálint . Halász-Dajka B. Synthesis  2006,  2625 
  • 3a Nijhuis WHN. Verboom W. Reinhoudt DN. Harkema S. J. Am. Chem. Soc.  1987,  109:  3136 
    Search in Google Scholar
  • 3b Groenen LC. Verboom W. Nijhuis WHN. Reinhoudt DN. Van Hummel GJ. Feil D. Tetrahedron  1988,  44:  4637 
    Search in Google Scholar
  • 3c Nijhuis WHN. Verboom W. El-Fadl AA. Harkema S. Reinhoudt DN. J. Org. Chem.  1989,  54:  199 
    Search in Google Scholar
  • 3d Nijhuis WHN. Verboom W. El-Fadl AA. Van Hummel GJ. Reinhoudt DN. J. Org. Chem.  1989,  54:  209 
    Search in Google Scholar
  • 3e Ojea V. Muinelo I. Figueroa MC. Ruiz M. Quintela JM. Synlett  1995,  622 
  • 3f Tverdokhlebov AV. Gorulya AP. Tolmachev AA. Kostyuk AN. Chernega AN. Rusanov EB. Tetrahedron  2006,  62:  9146 
    Search in Google Scholar
  • 4a Mátyus P. Fuji K. Tanaka K. Heterocycles  1994,  37:  171 
    Search in Google Scholar
  • 4b Schwartz A. Beke G. Kővári Z. Böcskey Z. Farkas . Mátyus P. J. Mol. Struct.  2000,  528:  49 
    Search in Google Scholar
  • 4c Károlyházy L. Regdon G. Éliás O. Beke G. Tábi T. Hódi K. Erős I. Mátyus P. J. Mol. Struct.  2003,  666-667:  667 
    Search in Google Scholar
  • 4d Kaval N. Dehaen W. Mátyus P. Van Der Eycken E. Green Chem.  2004,  6:  125 
    Search in Google Scholar
  • 4e Kaval N. Halasz-Dajka B. Vo-Thanh G. Dehaen W. Van Der Eycken J. Mátyus P. Loupy A. Van Der Eycken E. Tetrahedron  2005,  61:  9052 
    Search in Google Scholar
  • 4f Dajka-Halász B. Földi A. Ludányi K. Mátyus P. ARKIVOC  2008,  (iii):  102 
    Search in Google Scholar
  • 5a Devi I. Baruah B. Bhuyan PJ. Synlett  2006,  2593 
  • 5b Paramonov IV. Belyaev NA. Glukhareva TV. Volkov AS. Deeva EV. Morzherin YY. Chem. Heterocycl. Compd.  2006,  42:  127 
    Search in Google Scholar
  • 5c Ivanov IC. Glasnov TN. Belaj F. J. Heterocycl. Chem.  2008,  45:  177 
    Search in Google Scholar
  • 5d Ryabtsova OY. Pozharskii AF. Degtyarev AV. Ozeryanskii VA. Mendeleev Commun.  2006,  313 
  • 5e Povalyakhina MA. Pozharskii AF. Dyablo OV. Ozeryanskii VA. Ryabtsova OV. Mendeleev Commun.  2010,  20:  36 
    Search in Google Scholar
  • 6a Meth-Cohn O. Taylor DL. J. Chem. Soc., Chem. Commun.  1995,  1463 
  • 6b Cheng Y. Meth-Cohn O. Taylor D. J. Chem. Soc., Perkin Trans. 1  1998,  1257 
  • 7a Polonka-Bálint . Saraceno C. Ludányi K. Bényei A. Mátyus P. Synlett  2008,  2846 
  • 7b Dunkel P. Túrós G. Bényei A. Ludányi K. Mátyus P. Tetrahedron  2010,  66:  2331 
    Search in Google Scholar
  • 8 Sancho R. Medarde M. Sánchez-Palomino S. Madrigal BM. AlcamI J. Muñoz E. San Feliciano A. Bioorg. Med. Chem. Lett.  2004,  14:  4483 
    CrossrefSearch in Google Scholar
  • 9a Germuth FG. J. Am. Chem. Soc.  1929,  51:  1555 
    Search in Google Scholar
  • 9b Alder RW. Bryce MR. Goode NC. J. Chem. Soc., Perkin Trans. 2  1982,  477 
  • 10 Kirby AJ. Percy JM. Tetrahedron  1988,  44:  6903 
    CrossrefSearch in Google Scholar
  • 11a O’Leary J. Formosa X. Skranc W. Wallis JD. Org. Biomol. Chem.  2005,  3:  3273 
    Search in Google Scholar
  • 11b Bell PC. Wallis JD. Chem. Commun.  1999,  257 
  • 12 Bailey RJ. Card PJ. Shechter H. J. Am. Chem. Soc.  1983,  105:  6096 
    CrossrefSearch in Google Scholar
  • 13 Altomare A. Cascarano G. Giacovazzo C. Guagliardi A. J. Appl. Crystallogr.  1993,  26:  343 
    CrossrefSearch in Google Scholar
  • 14 Sheldrick GM. Programs for Crystal Structure Analysis (Release 97-2)   Göttingen; Germany: 1998. 
  • 15 Farrugia LJ. J. Appl. Crystallogr.  1999,  32:  837 
    CrossrefSearch in Google Scholar
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The X-ray data are available from the Cambridge Crystallographic Data Centre CCDC under the numbers 5: 7770044, 7: 777045, 10: 777046, 11: 777047, 15: 777048, respectively. Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK; fax: +44 (1223)336033 or e-mail: deposit@ccdc.cam.ac.uk. The details of the X-ray structures will be published elsewhere.

17

Experimental data are available in Supporting Information.