An easy synthetic approach to pyridoporphyrins by domino reactions

被引:31
作者
Alonso, Cristina M. A. [1 ]
Serra, Vanda I. V.
Neves, Maria G. P. M. S.
Tome, Augusto C.
Silva, Artur M. S.
Paz, Filipe A. A.
Cavaleiro, Jose A. S.
机构
[1] Univ Aveiro, Dept Chem, P-3810193 Aveiro, Portugal
[2] Univ Aveiro, CICECO, Dept Chem, P-3810193 Aveiro, Portugal
关键词
D O I
10.1021/ol070601w
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
beta-Amino-meso-tetraarylporphyrins react with cyclic enol ethers to yield pyrido[2,3-b]porphyrins bearing two vicinal hydroxyalkyl groups. These reactions are catalyzed by lanthanum triflate and occur under mild conditions. Esterification of the hydroxyalkyl groups with succinic anhydride and dodecanoyl chloride afforded the corresponding esters in almost quantitative yields. The crystal structure of the most hydrophobic derivative 7 was determined, and it shows that these porphyrinic macrocycles form one-dimensional supramolecular tapes in the solid state.
引用
收藏
页码:2305 / 2308
页数:4
相关论文
共 24 条
[1]   Applications of the Cambridge Structural Database in organic chemistry and crystal chemistry [J].
Allen, FH ;
Motherwell, WDS .
ACTA CRYSTALLOGRAPHICA SECTION B-STRUCTURAL SCIENCE CRYSTAL ENGINEERING AND MATERIALS, 2002, 58 :407-422
[2]   The Cambridge Structural Database: a quarter of a million crystal structures and rising [J].
Allen, FH .
ACTA CRYSTALLOGRAPHICA SECTION B-STRUCTURAL SCIENCE, 2002, 58 (3 PART 1) :380-388
[3]   β-Imino-meso-tetraphenylporphyrin derivatives in hetero-Diels-Alder reactions [J].
Alonso, CMA ;
Neves, MGPMS ;
Tomé, AC ;
Silva, AMS ;
Cavaleiro, JAS .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2004, 2004 (15) :3233-3239
[4]   Hetero-Diels-Alder reactions of β-imino-meso-tetraphenylporphyrin derivatives:: a new approach to pyrido[2,3-b]porphyrins [J].
Alonso, CMA ;
Neves, MGPMS ;
Tomé, AC ;
Silva, AMS ;
Cavaleiro, JAS .
TETRAHEDRON LETTERS, 2001, 42 (47) :8307-8309
[5]   Dysprosium(III) catalyzed formation of hexahydrofuro[3,2-c]quinolines via 2:1 coupling of dihydrofuran with substituted anilines [J].
Batey, RA ;
Powell, DA ;
Acton, A ;
Lough, AJ .
TETRAHEDRON LETTERS, 2001, 42 (45) :7935-7939
[6]   Cycloaddition reactions of porphyrins [J].
Cavaleiro, JAS ;
Neves, MGPMS ;
Tomé, AC .
ARKIVOC, 2003, :107-130
[7]   Domino reaction of anilines with 3,4-dihydro-2H-pyran catalyzed by cation-exchange resin in water: an efficient synthesis of 1,2,3,4-tetrahydroquinoline derivatives [J].
Chen, L ;
Li, CJ .
GREEN CHEMISTRY, 2003, 5 (05) :627-629
[8]  
Chen L, 2003, SYNLETT, P732
[9]   Uncatalysed domino reaction in hexafluoroisopropanol:: A simple protocol for the synthesis of tetrahydroquinoline derivatives [J].
Di Salvo, A ;
Spanedda, MV ;
Ourévitch, M ;
Crousse, B ;
Bonnet-Delpon, D .
SYNTHESIS-STUTTGART, 2003, (14) :2231-2235
[10]   Diels-Alder reactions of beta-vinyl-meso-tetraphenylporphyrin with quinones [J].
Faustino, MAF ;
Neves, MGPMS ;
Tomé, AC ;
Silva, AMS ;
Cavaleiro, JAS .
ARKIVOC, 2005, :332-343