Photochemical Approach to Naphthoxazoles and Fused Heterobenzoxazoles from 5-(Phenyl/heteroarylethenyl)oxazoles

被引:32
作者
Sagud, Ivana [1 ]
Faraguna, Fabio [1 ]
Marinic, Zeljko [2 ]
Sindler-Kulyk, Marija [1 ]
机构
[1] Univ Zagreb, Dept Organ Chem, Fac Chem Engn & Technol, Zagreb 10000, Croatia
[2] Rudjer Boskovic Inst, NMR Ctr, Zagreb 10000, Croatia
关键词
ALPHA; BETA-UNSATURATED ALDEHYDES; FURAN-DERIVATIVES; O-DIVINYLBENZENES; INHIBITORS; OXAZOLE; RING;
D O I
10.1021/jo1025942
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A new synthetic approach is presented for the synthesis of naphthoxazoles and fused heterobenzoxazoles. The starting 5-(aryl/furyl/thienyl/pyridyl ethenyl)oxazoles are prepared from the corresponding alpha,beta-unsaturated aldehydes using Van Leusen reagent in very good yields and are transformed into naphthoxazoles and fused heterobenzoxazoles on irradiation under aerobic conditions and in the presence of iodine.
引用
收藏
页码:2904 / 2908
页数:5
相关论文
共 42 条
[1]   New nitrogenated siloxy butadienes from 1,3-dichloroacetone [J].
Alonso, Dulce ;
Caballero, Esther ;
Medarde, Manuel ;
Tome, Fernando .
TETRAHEDRON LETTERS, 2007, 48 (06) :907-910
[2]   Dipeptidyl peptidase IV inhibitors derived from β-aminoacylpiperidines bearing a fused thiazole, oxazole, isoxazole, or pyrazole [J].
Ashton, WT ;
Sisco, RM ;
Hong, D ;
Lyons, KA ;
He, HB ;
Doss, GA ;
Leiting, B ;
Patel, RA ;
Wu, JK ;
Marsilio, F ;
Thornberry, NA ;
Weber, AE .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2005, 15 (09) :2253-2258
[3]   Photochemical formation of novel pyrrolo[3,2-b]-6,7-benzobicyclo[3.2.1]octa-2,6-diene [J].
Basaric, N ;
Marinic, E ;
Sindler-Kulyk, M .
JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (19) :7524-7527
[4]   Photochemistry of o-pyrrolylstilbenes and formation of spiro-2H-pyrroles and their rearrangement to dihydroindoles [J].
Basaric, Nikola ;
Marinic, Zeljko ;
Sindler-Kulyk, Marija .
JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (25) :9382-9392
[5]  
Bheemashankar A. K., 1999, TETRAHEDRON LETT, V40, P5633
[6]   A Mild and Convenient Synthesis of 4-Tosyl-4,5-dihydrooxazoles [J].
Companyo, Xavier ;
Moyano, Albert ;
Rios, Ramon .
LETTERS IN ORGANIC CHEMISTRY, 2009, 6 (04) :293-296
[7]   The unsaturation and tautomeric mobility of heterocyclic compounds Part XI alpha- and beta-naphthoxazole and 5-bromobenzoxazole derivatives - The ultra-violet absorption spectra of some tautomeric selenazoles [J].
Desai, RD ;
Hunter, RF ;
Khalidi, ARK .
JOURNAL OF THE CHEMICAL SOCIETY, 1938, :321-329
[8]   The TosMIC approach to 3-(oxazol-5-yl) indoles: Application to the synthesis of indole-based IMPDH inhibitors [J].
Dhar, TGM ;
Shen, ZQ ;
Fleener, CA ;
Rouleau, KA ;
Barrish, JC ;
Hollenbaugh, DL ;
Iwanowicz, EJ .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2002, 12 (22) :3305-3308
[9]   ALPHA,BETA-UNSATURATED ALDEHYDES BY ONE-STEP VINYLOGATION OF CARBONYL-COMPOUNDS [J].
DUHAMEL, L ;
PLE, G ;
CONTRERAS, B .
ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 1986, 18 (04) :219-226
[10]   Oxacyanines [J].
Fisher, NI ;
Hamer, FM .
JOURNAL OF THE CHEMICAL SOCIETY, 1934, :962-965