Green Method for the Synthesis of Benzo[f]pyrimido[4,5-b]quinoline Derivatives Catalyzed by Iodine in Aqueous Media

REFERENCES

• (a) Vijjay , N. C. ; Rajesh , A. U. ; Vinod , S. ; Bindu , A. R. ; Sreekanth , J. S. ; Lakshmi , B. Strategies for heterocyclic construction via novel multi-component reactions based on isocyanides and nucleophilic carbenes . Acc. Chem. Res. 2003 , 36 , 899 – 907 ; (b) Anary-Abbasinejad , M. ; Saidipoor , A. One-pot, four-component reaction of aryl aldehydes, aryl ketones, phosphorus trichloride, and acetonitrile catalyzed by acetyl chloride: Synthesis of β-acetamido ketones . Synth. Commun. 2008 , 38 , 354 – 360 ; (c) Tietze , L. F. Domino reactions in organic synthesis . Chem. Rev. 1996 , 96 , 115 – 136 ; (d) Bunce , R. A. Recent advances in the use of tandem reactions for organic synthesis . Tetrahedron 1995 , 51 , 13103 – 13159 ; (e) Hatamjafari , F. New protocol to synthesize spiro-1,4-dihydropyridines by using a multicomponent reaction of cyclohexanone, ethyl cyanoacetate, isatin, and primary amines under microwave irradiation . Synth. Commun. 2006 , 36 , 3563 – 3570 ; (f) Wang , X. S. ; Zhang , M. M. ; Jiang , H. ; Shi , D. Q. ; Tu , S. J. ; Wei , X. Y. ; Zong , Z. M. An improved and benign synthesis of 9,10-diarylacridin-1,8-dione and indenoquinoline derivatives from 3-arylamino-5,5-dimethyl cyclohex-2-enone, arylaldehyde and 1,3-dicarbonyl compound in ionic liquid medium . Synthesis 2006 , 4187 – 4199 ; (g) Wang , X. S. ; Zhang , M. M. ; Li , Q. ; Yao , C. S. ; Tu , S. J. An unexpected ring-opening of 2-pyrone ring in the synthesis of 1-arylbenzo[f]quinoline-2-carboxmide derivatives in aqueous media catalyzed by TEBAC . Synlett 2007 , (20) , 3141 – 3144 .
   PubMed Web of Science ®Google Scholar
• (a) Ahluwalia , V. K. ; Sahay , R. ; Das , U. Synthesis and antimicrobial activity of 1,3,5-triaryl-10-benzyl-1,2,3,4,6,7,8,9-octahydro-8,8-dimethyl-4,6-dioxo-2-thioxo-5 h,10 h-pyrimido[4,5-b]quinolines. Indian J. Chem. Sect. B 1999, 38, 1136–1138; (b) Kumar , R. N. ; Suresh , T. ; Mohan , P. S. Synthesis and antibacterial activity of pyrimido[4,5-b]quinolines. Indian J. Chem. Sect. B 2003, 42, 688–689.
   Google Scholar
• Kumar , R. N. ; Suresh , T. ; Mohan , P. S. A simple one-pot synthesis of 4-phenyl-3-oxopyrimido[4,5-b]quinolines and their biocidal studies . Asian J. Chem. 2002 , 14 , 1405 – 1408 .
   Web of Science ®Google Scholar
• Vishwanathan , C. L. ; Arun , J. A. ; Suresh , N. S. A Process for the synthesis of substituted 2,4,5-triamino-8-chloropyrimido-[4,5-b]quinolines as novel antimalarials . Indian Pat. IN 2003MU00627 A. 2005 .
   Google Scholar
• Naby , H. A. A. ; Mekheimer , R. A. ; Abd-Elhameed , A. M. ; Sadek , K. U. A Convenient one-pot synthesis of pyrimido[4,5-b]quinolines as 5-deaza non-classical antifolate inhibitors . J. Chem. Res. 1999 , ( 11 ), 678 – 679 .
   Web of Science ®Google Scholar
• Dorjsuren , D. ; Burnette , A. ; Gray , G. N. ; Chen , X. L. ; Zhu , W. M. ; Roberts , P. E. ; Currens , M. J. ; Shoemaker , R. H. ; Ricciardi , R. P. ; Sei , S. Chemical library screen for novel inhibitors of kaposi's sarcoma-associated herpesvirus processive DNA synthesis . Antiviral Res. 2006 , 69 , 9 – 23 .
   PubMed Web of Science ®Google Scholar
• (a) Kozlov , N. G. ; Basalaeva , L. I. Reaction of hexahydropyirimidine-2,4,6-trione with naphthalen-2-amine and benzaldehydes . Russ. J. Org. Chem. 2007 , 43 , 432 – 438 ; (b) Ryabukhin , S. V. ; Plaskon , A. S. ; Volochnyuk , D. M. ; Shivanyuk , A. N. ; Tolmachev , A. A. A one-pot fusion of nitrogen-containing heterocycles . Synthesis 2007 , ( 18 ), 2872 – 2886 ; (c) Li , S.-Y. ; Chen , Y.-L. ; Wang , C. ; Tzeng , C.-C. Synthesis and antiproliferative evaluation of certain pyrido[3,2-g]quinoline derivatives . Bioorg. Med. Chem. 2006 , 14 ( 22 ), 7370 – 7376 ; (d) Chao , W. ; Mahajan , Y. R. ; Weinreb , S. M. An approach to total synthesis of the cylindricine b pyridoquinoline subclass of tricyclic marine ascidian alkaloids . Tetrahedron Lett. 2006 , 47 ( 23 ), 3815 – 3818 ; (e) Tverdokhlebov , A. V. ; Gorulya , A. P. ; Tolmachev , A. A. ; Kostyuk , A. N. ; Chernega , A. N. ; Rusanov , E. B. The tert-amino effect in the synthesis of hetaryl- and arylsulfonyl-substituted pyrrolo- and pyrido[1,2-a]quinoline derivatives and their pyrazolo annulated analogues . Synthesis 2005 , (13) , 2161 – 2170 .
   Web of Science ®Google Scholar
• Wang , X. S. ; Zhang , M. M. ; Zeng , Z. S. ; Shi , D. Q. ; Tu , S. J. ; Wei , X. Y. ; Zong , Z. M. A new synthesis method for benzo[f]quinolin-3-carbonyl urea and thiourea derivatives in aqueous media catalyzed by TEBAC. J. Heterocycl. Chem. 2007, 44, 441–447.
   Web of Science ®Google Scholar