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Synthesis 2007(14): 2208-2214  
DOI: 10.1055/s-2007-983764
PAPER
© Georg Thieme Verlag Stuttgart · New York

Synthesis of the 4,10-Dihydro-3H-pyridazino[1,6-b]isoquinolin-10-one System by a Furan Recyclization Reaction

Alexander V. Butin*a, Artem S. Dmitrieva, Olga N. Kostyukovaa, Vladimir T. Abaevb, Igor V. Trushkovc
a Research Institute of Heterocyclic Compounds Chemistry, Kuban State University of Technology, Moskovskaya St. 2, Krasnodar 350072, Russian Federation
Fax: +7(861)2596592; e-Mail: alexander_butin@mail.ru; e-Mail: av_butin@yahoo.com;
b North-Ossetian State University, Vatutina St. 46, Vladikavkaz 362025, Russian Federation
c Department of Chemistry, M.V. Lomonosov Moscow State University, Leninskie Gory 1/3, Moscow 119992, Russian Federation
Further Information

Publication History

Received 27 April 2007
Publication Date:
03 July 2007 (online)

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Abstract

The novel 4,10-dihydro-3H-pyridazino[1,6-b]isoquinolin-10-one heterocyclic system was synthesized by acid-catalyzed recyclization of 2-(difurylmethyl)benzohydrazides as well as by recyclization of (2-carboxyaryl)difurylmethanes to isocoumarins followed by the reaction with hydrazine hydrate.

Key words

furans - ring opening - ring closure - fused-ring system - pyridazino[1,6-b]isoquinolinone

    References

  • For reviews, see:
  • 1a Dean FM. Adv. Heterocycl. Chem.  1982,  30:  167 
    CrossrefSearch in Google Scholar
  • 1b Dean FM. Adv. Heterocycl. Chem.  1982,  31:  237 
    CrossrefSearch in Google Scholar
  • 1c Kappe CO. Murphree SS. Padwa A. Tetrahedron  1997,  53:  14179 
    CrossrefSearch in Google Scholar
  • 1d Ciufolini MA. Hermann CYW. Dong Q. Shimizu T. Swaminathan S. Xi N. Synlett  1998,  105 
    Crossref
  • 1e Butin AV. Abaev VT. Stroganova TA. Gutnov AV. In Targets in Heterocyclic Systems: Chemistry and Properties   Vol. 5:  Attanasi O. A. Spinelli D. Italian Society of Chemistry; Rome: 2001.  p.131 
    CrossrefSearch in Google Scholar
  • 1f Zubkov FI. Nikitina EV. Varlamov AV. Russ. Chem. Rev. (Engl. Transl.)  2005,  74:  639 ; Usp. Khim. 2005, 74, 707
    CrossrefSearch in Google Scholar
  • 2 For a review, see: Piancatelli G. D’Auria M. D’Onofrio F. Synthesis  1994,  867 
    Thieme Connect
  • 3a Bezoari MD. Paudler WW. J. Org. Chem.  1980,  45:  4584 
    Search in Google Scholar
  • 3b Haley JF. Rosenfeld SM. Keehn PM. J. Org. Chem.  1977,  42:  1379 
    Search in Google Scholar
  • 3c Kharchenko VG. Markushina IA. Voronin SP. Chem. Heterocycl. Compd. (Engl. Transl.) 1982, 18, 318; Khim. Geterotsikl. Soedin.  1982,  418 
  • 3d Kharchenko VG. Gubina TI. Voronin SP. Markushina IA. Chem. Heterocycl. Compd. (Engl. Transl.) 1986, 22, 1170; Khim. Geterotsikl. Soedin.  1986,  1453 
  • 3e Voronin SP. Gubina TI. Markushina IA. Kharchenko VG. Chem. Heterocycl. Compd. (Engl. Transl.) 1989, 25, 1113; Khim. Geterotsikl. Soedin.  1989,  1333 
  • See for example:
  • 4a Skvortsov IM. Buntyakova NA. Kuramshin MI. Filimonov SA. Chem. Heterocycl. Compd. (Engl. Transl.) 1983, 19, 1139; Khim. Geterotsikl. Soedin.  1983,  1424 
    Thieme Connect
  • 4b Stroganova TA. Butin AV. Vasilin VK. Nevolina TA. Krapivin GD. Synlett  2007,  1106 
    Thieme Connect
  • 5 For a review, see: Butin AV. Abaev VT. Russ. Chem. Bull. (Engl. Transl.) 2001, 50, 1510; Izv. Akad. Nauk SSSR, Ser. Khim.  2001,  1436 
  • 6a Butin AV. Krapivin GD. Zavodnik VE. Kul’nevich VG. Chem. Heterocycl. Compd. (Engl. Transl.) 1993, 29, 524; Khim. Geterotsikl. Soedin.  1993,  616 
    Crossref
  • 6b Abaev VT. Gutnov AV. Butin AV. Chem. Heterocycl. Compd. (Engl. Transl.) 1998, 34, 529; Khim. Geterotsikl. Soedin.  1998,  603 
    Crossref
  • 6c Gutnov AV. Butin AV. Abaev VT. Krapivin GD. Zavodnik VE. Molecules  1999,  4:  204 
    CrossrefSearch in Google Scholar
  • 7a Butin AV. Stroganova TA. Lodina IV. Krapivin GD. Tetrahedron Lett.  2001,  42:  2031 
    CrossrefSearch in Google Scholar
  • 7b Butin AV. Smirnov SK. Stroganova TA. J. Heterocycl. Chem.  2006,  43:  623 
    CrossrefSearch in Google Scholar
  • 7c Butin AV. Smirnov SK. Stroganova TA. Bender W. Krapivin GD. Tetrahedron  2007,  63:  474 
    CrossrefSearch in Google Scholar
  • 8a Gutnov AV. Abaev VT. Butin AV. Dmitriev AS. J. Org. Chem.  2001,  66:  8685 
    CrossrefSearch in Google Scholar
  • 8b Dmitriev AS. Podelyakin SA. Abaev VT. Butin AV. Chem. Heterocycl. Compd. (Engl. Transl.) 2005, 41, 1194; Khim. Geterotsikl. Soedin.  2005,  1400 
    Crossref
  • 8c Abaev VT. Dmitriev AS. Gutnov AV. Podelyakin SA. Butin AV. J. Heterocycl. Chem.  2006,  43:  1195 
    CrossrefSearch in Google Scholar
  • 9 Abaev VT. Osipova AA. Butin AV. Chem. Heterocycl. Compd. (Engl. Transl.) 2001, 37, 785; Khim. Geterotsikl. Soedin.  2001,  849 
  • 10 Butin AV. Abaev VT. Mel’chin VV. Dmitriev AS. Tetrahedron Lett.  2005,  46:  8439 
    CrossrefSearch in Google Scholar
  • 11 Butin AV. Dmitriev AS. Abaev VT. Zavodnik VE. Synlett  2006,  3431 
    Thieme Connect
  • 12 Johnstone RWA. Rose ME. Tetrahedron  1979,  35:  2169 
    CrossrefSearch in Google Scholar
  • 13a Ferrer S. Naughton DP. Parveen I. Threadgill MD. J. Chem. Soc., Perkin Trans. 1  2002,  335 
  • 13b Ukita T. Nakamura Y. Kubo A. Yamamoto Y. Moritani Y. Saruta K. Higashijima T. Kotera J. Takagi M. Kikkawa K. Omori K. J. Med. Chem.  2001,  44:  2204 
    Search in Google Scholar
  • 13c Kowalczyk BA. Synthesis  2000,  1113 
  • 13d Yamaguchi S. Uchiuzoh Y. Sanada K. J. Heterocycl. Chem.  1995,  32:  419 
    Search in Google Scholar
  • 13e Bhide BH. Akolkar VD. Brahmbhatt DI. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem.  1993,  32:  675 
    Search in Google Scholar
  • 14 Cushman M. Jayaraman M. Vroman JA. Fukunaga AK. Fox BM. Kohlhagen G. Strumberg D. Pommier Y. J. Med. Chem.  2000,  43:  3688 
    CrossrefSearch in Google Scholar
  • 15 Dusemund J. Arch. Pharm.  1982,  315:  925 
    CrossrefSearch in Google Scholar