Molecular Iodine–Catalyzed One-Pot Synthesis of Tetrahydrobenzo[a]xanthene-11-one and Diazabenzo[a]anthracene-9,11-dione Derivatives

REFERENCES

• Hideo , T. ; Teruomi , J. (Sankyo Co.) Benzopyrano[2,3-b]xanthene derivatives and its preparation. Jpn. Patent 56005480, 1981.
   Google Scholar
• Poupelin , J. P. ; Saint-Ruf , G. ; Foussard-Blanpin , O. ; Marcisse , G. ; Uchida-Ernouf , G. ; Lacroix , R. Synthesis and anti-inflammatory properties of bis(2-hydroxy-1-naphthyl)methane derivatives, I: Monosubstituted derivatives . Eur. J. Med. Chem. 1978 , 13 , 67 .
   Web of Science ®Google Scholar
• Lambert , R. W. ; Martin , J. A. ; Merrett , J. H. ; Parkes , K. E. B. ; Thomas , G. J. Pyrimidine nucleosides. PCT Int. Appl. WO9706178, 1997.
   Google Scholar
• Saint-Ruf , G. ; De , A. ; Hieu , H. T. ; Poupelin , J. P. Effect of dibenzoxanthenes on paralyzing action of zoxazolamine . Naturwissenschaften 1975 , 62 , 584 .
   PubMed Web of Science ®Google Scholar
• Ion , R. M. ; Frackowiak , D. ; Planner , A. ; Wiktorowicz , K. The incorporation of various porphyrins into blood cells measured via flow cytometry, absorption, and emission spectroscopy . Acta Biochim. Pol. 1998 , 45 , 833 .
   PubMed Web of Science ®Google Scholar
• (a) Banerjee , A. ; Mukherjee , A. K. Chemical aspects of santalin as a histological stain . Stain. Technol. 1981 , 56 , 83 ; (b) Menchen , S. M. ; Benson , S. C. ; Lam , J. Y. L. ; Zhen , W. ; Sun , D. ; Rosenblum , B. B. ; Khan , S. H. ; Taing , M. Sulfonated diarylrhodamine dyes. U.S. Patent 6,583,168, 2003 .
   PubMed Web of Science ®Google Scholar
• Knight , C. G. ; Stephens , T. Xanthene-dye-labelled phosphatidylethanolamines as probes of interfacial pH: Studies in phospholipid vesicles. Biochem. J. 1989, 258, 683.
   PubMed Web of Science ®Google Scholar
• (a) Siirkecioglu , O. ; Talini , N. ; Akar , A. Synthesis of 24-alkyl-14H-dibenzo[a,j]xanthenes . J. Chem. Res., Synop. 1995 , 502 (b) Ahmad , M. ; King , T. A. ; Ko , D.-K. ; Cha , B. H. ; Lee , J. Performance and photostability of xanthene and pyrromethene laser dyes in solgel phases . J. Phys. D: Appl. Phys. 2002 , 35 , 1473 .
   Google Scholar
• Li , J. ; Tang , W. ; Lu , L. ; Su , W. Strontium triflate catalyzed one-pot condensation of β-naphthol, aldehydes and cyclic 1,3-dicarbonyl compounds . Tetrahedron Lett. 2008 , 49 , 7117 .
   Web of Science ®Google Scholar
• Das , B. ; Laxminarayana , K. ; Krishnaiah , M. ; Srinivas , Y. An efficient and convenient protocol for the synthesis of novel 12-aryl- or 12-alkyl-8,9,10,12-tetrahydrobenzo[a]xanthen-11-one derivatives . Synlett 2007 , 3107 .
   Web of Science ®Google Scholar
• Jitender , M. K. ; Devanshi , M. pTSA-catalyzed one-pot synthesis of 12-aryl-8,9,10,12-tetrahydrobenzo[a]xanthen-11-ones in ionic liquid and neat conditions . Tetrahedron Lett. 2009 , 50 , 4777 .
   Web of Science ®Google Scholar
• Nandi , G. C. ; Samai , S. S. ; Kumar , R. ; Singh , M. S. An efficient one-pot synthesis of tetrahydrobenzo[a]xanthene-11-one and diazabenzo[a]anthracene-9-11-dione derivatives under solvent free condition . Tetrahedron 2009 , 65 , 7129 .
   Web of Science ®Google Scholar
• (a) Kim , K. M. ; Ryu , E. K. Unusual iodine-catalyzed lactonization of γ-methyl-γ,δ-pentenoic acids: A facile synthesis of γ,γ-dimethyl-γ-butyrolactones . Tetrahedron Lett. 1996 , 37 , 1441 ; (b) Firouzabadi , H. ; Iranpoor , N. ; Hazarkhani , H. Iodine catalyzes efficient and chemoselective thioacetalization of carbonyl functions, transthioacetalization of O,O- and S,O-acetals and acylals . J. Org. Chem. 2001 , 66 , 7527 ; (c) Ramalinga , K. ; Vijayalakshmi , P. ; Kaimal , T. N. B. A mild and efficient method for esterification and transesterification catalyzed by iodine . Tetrahedron Lett. 2002 , 43 , 879 ; (d) Firouzabadi , H. ; Iranpoor , N. ; Sobhani , S. A high-yielding preparation of α-trimethylsilyloxyphosphonates by silylation of α-hydroxyphosphonates with HMDS catalyzed by iodine . Tetrahedron Lett. 2002 , 43 , 3653 ; (e) Yadav , J. S. ; Reddy , B. V. S. ; Reddy , M. S. ; Prasad , A. R. Iodine as novel reagent for the 1,2-addition of trimethylsilyl cyanide to ketones including α, β-unsaturated ketones . Tetrahedron Lett. 2002 , 43 , 9703 ; (f) Bandgar , B. P. ; Shaikh , K. A. Molecular iodine–catalyzed efficient and highly rapid synthesis of bis(indolyl)methanes under mild conditions . Tetrahedron Lett. 2003 , 44 , 1959 ; (g) Das , B. ; Banerjee , J. ; Ramu , R. ; Pal , R. ; Ravindranath , N. ; Ramesh , C. Efficient, selective deprotection of aromatic acetates catalyzed by amberlyst-15 or iodine . Tetrahedron Lett. 2003 , 44 , 5465 ; (h) Saeeng , R. ; Sirion , U. ; Sahakitpichan , P. ; Isobe , M. Iodine catalyzes C-glycosidation of d-glucal with silylacetylene . Tetrahedron Lett. 2003 , 44 , 6211 ; (i) Ji , S.-J. ; Wang , S.-Y. ; Zhang , Y. ; Loh , T.-P. Facile synthesis of bis(indolyl)methanes using catalytic amount of iodine at room temperature under solvent-free conditions . Tetrahedron 2004 , 60 , 2051 ; (j) Yadav , J. S. ; Reddy , B. V. S. ; Shubashree , S. ; Sadashiv , K. Iodine/MeOH: A novel and efficient reagent system for thiocyanation of aromatics and heteroaromatics . Tetrahedron Lett. 2004 , 45 , 2951 ; (k) Phukan , P. Iodine as a very powerful catalyst for three component synthesis of protected homoallylic amines . J. Org. Chem. 2004 , 69 , 4005 ; (l) Phukan , P. Iodine as an extremely powerful catalyst for the acetylation of alcohols under solvent-free conditions . Tetrahedron Lett. 2004 , 45 , 4785 ; (m) Sun , J. ; Dong , Y. ; Wang , X. ; Wang , S. ; Hu , Y. Highly Efficient chemoselective deprotection of O,O-acetals and O,O-ketals catalyzed by molecular iodine in acetone . J. Org. Chem. 2004 , 69 , 8932 ; (n) Bhosale , R. S. ; Bhosale , S. V. ; Wang , T. ; Zubaidha , P. K. An efficient, high-yielding protocol for the one-pot synthesis of dihydropyrimidin-2(1H)-ones catalyzed by iodine . Tetrahedron Lett. 2004 , 45 , 9111 ; (o) Ke , B. ; Qin , Y. ; He , Q. ; Huang , Z. ; Wang , F. Preparation of bisindolylalkanes from N-tert-butanesulfinyl aldimines . Tetrahedron Lett. 2005 , 46 , 1751 ; (p) Banik , B. K. ; Fernandez , M. ; Alvarez , C. Iodine-catalyzed highly efficient Michael reaction of indoles under solvent-free condition . Tetrahedron Lett. 2005 , 46 , 2479 .
   Web of Science ®Google Scholar