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Synthesis 2007(14): 2208-2214
DOI: 10.1055/s-2007-983764
DOI: 10.1055/s-2007-983764
PAPER
© Georg Thieme Verlag Stuttgart · New YorkSynthesis of the 4,10-Dihydro-3H-pyridazino[1,6-b]isoquinolin-10-one System by a Furan Recyclization Reaction
Further Information
Received
27 April 2007
Publication Date:
03 July 2007 (online)
Publication History
Publication Date:
03 July 2007 (online)
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
- For reviews, see:
- 1a
Dean FM. Adv. Heterocycl. Chem. 1982, 30: 167 - 1b
Dean FM. Adv. Heterocycl. Chem. 1982, 31: 237 - 1c
Kappe CO.Murphree SS.Padwa A. Tetrahedron 1997, 53: 14179 - 1d
Ciufolini MA.Hermann CYW.Dong Q.Shimizu T.Swaminathan S.Xi N. Synlett 1998, 105 - 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 - 1f
Zubkov FI.Nikitina EV.Varlamov AV. Russ. Chem. Rev. (Engl. Transl.) 2005, 74: 639 ; Usp. Khim. 2005, 74, 707 - 2 For a review, see:
Piancatelli G.D’Auria M.D’Onofrio F. Synthesis 1994, 867 - 3a
Bezoari MD.Paudler WW. J. Org. Chem. 1980, 45: 4584 - 3b
Haley JF.Rosenfeld SM.Keehn PM. J. Org. Chem. 1977, 42: 1379 - 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 - 4b
Stroganova TA.Butin AV.Vasilin VK.Nevolina TA.Krapivin GD. Synlett 2007, 1106 - 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 - 6b
Abaev VT.Gutnov AV.Butin AV. Chem. Heterocycl. Compd. (Engl. Transl.) 1998, 34, 529; Khim. Geterotsikl. Soedin. 1998, 603 - 6c
Gutnov AV.Butin AV.Abaev VT.Krapivin GD.Zavodnik VE. Molecules 1999, 4: 204 - 7a
Butin AV.Stroganova TA.Lodina IV.Krapivin GD. Tetrahedron Lett. 2001, 42: 2031 - 7b
Butin AV.Smirnov SK.Stroganova TA. J. Heterocycl. Chem. 2006, 43: 623 - 7c
Butin AV.Smirnov SK.Stroganova TA.Bender W.Krapivin GD. Tetrahedron 2007, 63: 474 - 8a
Gutnov AV.Abaev VT.Butin AV.Dmitriev AS. J. Org. Chem. 2001, 66: 8685 - 8b
Dmitriev AS.Podelyakin SA.Abaev VT.Butin AV. Chem. Heterocycl. Compd. (Engl. Transl.) 2005, 41, 1194; Khim. Geterotsikl. Soedin. 2005, 1400 - 8c
Abaev VT.Dmitriev AS.Gutnov AV.Podelyakin SA.Butin AV. J. Heterocycl. Chem. 2006, 43: 1195 - 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 - 11
Butin AV.Dmitriev AS.Abaev VT.Zavodnik VE. Synlett 2006, 3431 - 12
Johnstone RWA.Rose ME. Tetrahedron 1979, 35: 2169 - 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 - 13c
Kowalczyk BA. Synthesis 2000, 1113 - 13d
Yamaguchi S.Uchiuzoh Y.Sanada K. J. Heterocycl. Chem. 1995, 32: 419 - 13e
Bhide BH.Akolkar VD.Brahmbhatt DI. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 1993, 32: 675 - 14
Cushman M.Jayaraman M.Vroman JA.Fukunaga AK.Fox BM.Kohlhagen G.Strumberg D.Pommier Y. J. Med. Chem. 2000, 43: 3688 - 15
Dusemund J. Arch. Pharm. 1982, 315: 925