ࡱ> L bjbjss 8"]Z@@8,%s09:ssssNNN$E">E*NN**ss-*ss*s0C0s"t""$N&|<NNNNNNs****"NNNNNNNNN@ I: Photochemistry of supstituted 2- styryl oxazoles I. `agud1, }. Marini2, M.`indler-Kulyk 1)Department of Organic chemistry, Faculty of Chemical Engineering and Technology, University of Zagreb, Maruliev Trg 19, 10 000 Zagreb, Croatia HYPERLINK "mailto:isagud@fkit.hr"isagud@fkit.hr 2)NMR Center, The Ruer Boakovi Institute, bijeni ka cesta 54, Zagreb, Croatia Heterocycles have been studied in our group for a long period of time. Among them the field of my research are oxazoles. Oxazole is a five-membered ring compound with two heteroatoms, oxygen and nitrogen. Aromaticity of the ring is very weakened by its structure, this makes the ring reactive and the synthesis more complicated. Oxazole chemistry is extensive, it takes part in natural products, medicinal chemistry and material sciences []. It is required from chemistry in present days maximum yield products with minimum pollution. The best way of being in concordance with this is to utilise light as a very clean source of energy []. Starting compounds (Sheme 1) were prepared by Wittig reaction from aldehydes which were synthesized by formylation [] of substituted oxazole derivatives.  EMBED ChemDraw.Document.6.0  Sheme 1 Unlike the 5-styryl derivatives, photochemistry of which showed the intramolecular 2+2 cycloaddition and formation of bicyclo[2.1.1]hexene derivatives, 2-styryl derivatives undergo completely different photochemical process giving new and unexpected quinoline derivatives (Sheme 2).  EMBED ChemDraw.Document.6.0  Sheme 2 $:B`bhrt   8 : < @  ŵwlw_wWKhOemH nH sH tH hOemH sH h*nJhOe0JmH sH h *hOemH sH jhOeUh1IhOemH sH h1IhOeH*mH sH h1IhOeCJH*aJmH sH h1IhOeCJaJmH sH h)ShOeCJH*aJmH sH hOe>*CJaJmH sH h1IhOe>*CJaJmH sH h1IhOe5CJaJmH sH hOe5CJaJmH sH bX < * ^`acdfgijkl$a$gdOe$ P dha$gdOe $dha$gdOedhgdOe $dha$gdOe & ' ) ;GTWdeiȽȽȽȲȽtlllajN hOeUVhOemH sH jN hOeUVh *hOemH sH jhOeUh hOemH nH sH tH !jhd3hOe0JUmH sH hd3hOemH sH h1IhOemH sH hOemH sH hOemH nH sH tH )jhd3hOe0JUmH nH sH tH hd3hOemH nH sH tH "+,K\]^_abdeghjklm!&'(+,ôwod[U hOe0Jh1 hOe0JhchOemHsHhOemH sH h *hOe5mH sH h *hOe6mH sH h *hOemH sH hmH sH  hCJhjhUhOehOemH nH sH tH hOemH sH h1IhOemH sH U h hOehOemH nH sH tH hOejhOeUjhOeU!The structure determination of the products as well as reaction mechanisms will be discussed.     [1] D.C. Palmer, Oxazoles: Synthesis, Reactions, and Spectroscopy in E.C. Taylor, P. Wipf The Chemistry of heterocyclic compounds; Part A, John Wiley and Sons Inc., New Jersey 2003, 2-3. [2] A. Albini, M. Fagnoni, Green Chem. 6 (2004) 1-6. [] M. indler-Kulyk, D.Vojnovilm(^$ P dha$gdOegdOe,CMPR\]^_`bcflmrtuv $0<BDHPVnrz~ź}qihOemHsHh *hOe6mHsHh *hOe5mHsHh1IhOe6mH sH Uh1IhOemH sH jh1 hOe0JUh *hOemHsHhdhOemHsHhOeCJaJmHsHhg2hOe5CJaJmHsHhg2hOe6CJaJmHsHhg2hOeCJaJmHsH&, N. Defterderovi, }. Marini, D. Srzi, Heterocycles, 1994, 38, 1791. hOehOemH nH sH tH hhlhOemHsH61h:pBP. 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'7@ffe: (7B33^F )DOF *FH: +7NHeS 27QO`_ 47TH@l 6WmQw 8+7,TUs_MsƭU{# `OYOI 9[}; :] ;q ;+7>ςm 7ςm>t# `Nd_eeS A7g33^`_ C7j"0E E73R 4]1,]/6Z#`R1m%N G73R R%n4J%L2T#`R2H ,<> MII ->@ J .@B IfKK /BD L 0DF KPMM 1F< P 3DN S 5NQ PVV 7QT _ <TW ` =WY a >Y[ `olbb ?[] c @]T bV_f BBd i Ddgl F[j o HYm p63w6wW33 I&ChemDraw can't interpret this label.%       $ R1 = H, CH3, Ph R2 = H, CH3, Ph-CH3F DMHCGRTS '*  x( `2<&['([)<*+2;|4u6\ X8 F9 :;A[|C E UG,-./01357 < = > ? @ B D F H O NR1R2 ``     `` N  ``  Ws W; : `` h   %f            $  8I Y8  %R1 = H, CH3, Ph R2 = H, CH3, Ph-CH3ArialF\MMDLSKXY Ariald 0 X% ArialdArialdArialdArialdArialdArialdArialdArialdArialdArialdR1 =  H, CH3, Ph R2 =  H, CH3, Ph-CH3  0#!% l%CGD!% l%CkD!% @D}D!% Hm1DkD!% Hm1DGD!% @D5D!% ~PD5D!% poDGD!% QD5D!O% DoKD!% mDG7D!% _DtD!N% aDЪD!% ~PDo}D!% poDkD!% VDC!% 1QD]CD '(. ' '(. ' '(. ' ' '(. ' '  '  ' (. '  ' (. '  ' (. '  ' % % CONTENTSk _1321791915 !mA. 00Ole (EPRINT M`y$$?1,-e<O|. &7>33^|. '7@ffe: (7B33^F )DOF *FH: +7NHeS 27QO`_ 47TH@l 6WmQw 8+7,TUs_MsƭU{# `OYOI 9[}; :] ;q ;+7>ςm 7ςm>t# `Nd_eeS A7g33^`_ C7j"0E E73R 4]1,]/6Z#`R1m%N G73R R%n4J%L2T#`R2H ,<> MII ->@ J .@B IfKK /BD L 0DF KPMM 1F< P 3DN S 5NQ PVV 7QT _ <TW ` =WY a >Y[ `olbb ?[] c @]T bV_f BBd i Ddgl F[j o HYm p63w6wW33 I&ChemDraw can't interpret this label.%       $ R1 = H, CH3, Ph R2 = H, CH3, Ph-CH3Oh+'0h  $ 0 <HPX`IvanaNormalIvana1Microsoft Office Word@@l5z@l5zlh~<Z EMF  @@    W k KRp9Symbol? |||{||< |||((0?8?|H??| |dP\|??X|?l{|||||?|dv%   &% 6c % &% (  b  % ( '% &% 6W b  % ( '% (  % ( % &% c6  % &% (  b  % ( '%  % ( % &%  6c % &% (  b  % ( '% &% 6rW b  % ( '% (  % ( % &% c6 % &% (  b  % ( '%  % ( % &% 6  % &% (  b  % ( '% &% r6 b  % ( '% (  % ( % &%  6 % &% (  b  % ( '%  % ( % &% 6 % &% (  b  % ( '%  % ( % &% 6W % &% (  b  % ( '% &% 6W b  % ( '% (  % ( % &% W6 % &% (  b  % ( '%  % ( % &% c6 % &% (  b  % ( '%  % ( % &% 6Xb % &% (  b  % ( '% &% 6MP b  % ( '% ( Rp9"ArialxPh ?L||||?|@j0 OPX?X?|||||?|dv% %  % ( % Rp"Arial O(PX?6?|X?||||?|dv%  TT`,i;@~@LPO? % % _% _% _ TTX`@~@_LPN8 % &% 6 % &% (  _ % ( '%  % ( % &% A6 % &% (  _ % ( '%  % ( % &% 6]@ % &% (  _ % ( '% &% g6MU _ % ( '% (  % ( % &% ]@6 > % &% (  _ % ( '%  % ( % &% o6 % &% (  _ % ( '% &% v6 _ % ( '% ( % %  % ( % %  TTv~@~@LPR8 % Rpk"Arial|R,n@b@b@f|b@n@,PUUUUV@ OPX?@X?||||?|dv% Rp"ArialwTwwwT!^K %2XO,3Ok?Pb@ 0 |OPtX?0Xp ?b@||||?|dv%  TT@~@LP1& % % &% ]@6  % &% (   % ( '% % %  % ( % %  TT(7@~@LPR8 % %   %    TT.:@~@  LP2& % % &% 6 % &% (     % ( '% % % % % % % % y %  % ( % y % y  TT&e.t@~@y LPR8 % % % %  %   TT/j4v@~@ LP1& % % % y % y  TT5e8t@~@y LP  y  TT9e@t@~@y LP=2 6y  TT@eCt@~@6y LP  My  TTDeLt@~@My LPP8 y  TTMeSt@~@y LPh, % %  %   TT&t.@~@ LPR8 % % % %  %   TT/z4@~@ LP2& % % %  %   TT5t8@~@ LP    TT9t@@~@ LP=2 6  TT@tC@~@6 LP  M  TTDtL@~@M LPC8   TTNtV@~@ LPH8 % % % %  %   TTWz\@~@ LP3& % % %  %   TT]t`@~@ LP,   TT`tc@~@ LP    TTdtl@~@ LPP8 M  TTmts@~@M LPh, % % % V06?y!>!y!% % !6!% % V,;;$$% %  % %  M  % '%  % ( % &% 61 % &% (  M  % ( '% &% 6% M  % ( '% (  % ( % &% 16.m % &% (  M  % ( '%  % ( % &% .m61 % &% (  M  % ( '% &% .U6% M  % ( '% (  % ( % &% 16 % &% (  M  % ( '%  % ( % &% 6.~ % &% (  M  % ( '% &% 6. 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