Abstract
Reactions of 2,4,5-trimethyloxazole, 2,4,5-trimethylthiazole,
2-methylthiazole, and 2-ethyl-4,5-dimethylthiazole with different
acid chlorides in the presence of different bases were explored.
Arylvinyl esters of substituted benzoic acids containing substituted
oxazoles or thiazoles were formed when aroyl chlorides were used.
Degrees of aroylation were different with different bases. Reactions
with alkyl acid chlorides were also explored. Most of these reactions
occurred through cyclic ketene acetal intermediates.
Key words
carbon-carbon bond formation - oxazoles - thiazoles - vinyl esters - in situ generated
cyclic ketene acetal
References
1 Cao L.
Wu Z.
Zhu PC.
Polym.
Prepr.
1999,
39:
406
2 Cao L.
Wu Z.
Pittman CU.
J.
Polym. Sci., Part A: Polym. Chem.
1999,
37:
2841
3 Cao L.
Pittman CU.
J. Polym. Sci., Part
A: Polym. Chem.
1999,
37:
2823
4 Wu Z.
Cao L.
Pittman CU.
Recent
Res. Dev. Polym. Sci.
1998,
2:
467
5 Wu Z.
Cao L.
Pittman CU.
J.
Polym. Sci., Part A: Polym. Chem.
1998,
36:
861
6 Zhu PC.
Pittman CU.
J. Polym.
Sci., Part A: Polym. Chem.
1996,
34:
169
7 Wu Z.
Cao L.
Zhu PC.
Polym.
Prepr.
1997,
38:
121
8 Pittman CU.
Wu Z.
Zhu PC.
J. Polym. Sci., Part A: Polym. Chem.
1997,
35:
485
9 Zhu PC.
Pittman CU.
J. Polym.
Sci., Part A: Polym. Chem.
1996,
34:
73
10 Liu Y.
Pittman CU.
J. Polym. Sci., Part
A: Polym. Chem.
1997,
35:
3655
11 Gruseck U.
Heuschmann M.
Tetrahedron Lett.
1987,
28:
6027
12 Gruseck U.
Heuschmann M.
Chem. Ber.
1987,
120:
2065
13 Zhou A.
Pittman CU.
Tetrahedron
Lett.
2005,
46:
3801
14 Zhu PC.
Lin J.
Pittman CU.
J.
Org. Chem.
1995,
60:
5729
15 Cao L.
Ph.D. Dissertation
Mississippi
State University;
USA:
1999.
16 Li H.
MS Thesis
Mississippi
State University;
USA:
2005.
17 Ye G.
Ph.D. Dissertation
Mississippi
State University;
USA:
2008.
18 Ye G.
Henry WP.
Chen C.
Zhou A.
Pittman CU.
Tetrahedron
Lett.
2009,
50:
2135
19 Zhou A.
Cao L.
Li H.
Liu Z.
Pittman CU.
Synlett
2006,
201
20 Zhou A.
Cao L.
Li H.
Liu Z.
Cho H.
Henry WP.
Pittman CU.
Tetrahedron
2006,
62:
4188
21 Diaz-Ortiz AL.
Diez-Barra E.
de la Hoz A.
Prieto P.
Moreno A.
Langa F.
Prange T.
Neuman A.
J. Org. Chem.
1995,
60:
4160
22 Zhou A.
Ph.D. Dissertation
Mississippi
State University;
USA:
2004.
23 Tohda Y.
Kawashima T.
Ariga M.
Akiyama R.
Shudoh H.
Mori Y.
Bull. Chem. Soc. Jpn.
1984,
57:
2329
24 Zhou A.
Pittman CU.
Tetrahedron
Lett.
2004,
45:
8899
25 Zhou A.
Pittman CU.
Synthesis
2006,
37
26 Zhou A.
Pittman CU.
Tetrahedron
Lett.
2005,
46:
2045
27 Ye G.
Chen C.
Chatterjee S.
Collier WE.
Zhou A.
Song Y.
Beard DJ.
Pittman CU.
Synthesis
2010,
141
28 Ye G.
Chatterjee S.
Zhou A.
Barker BL.
Chen C.
Song Y.
Pittman CU.
Tetrahedron
2010,
66:
2919
29 Ye G.
Chatterjee S.
Zhou A.
Barker BL.
Chen C.
Song Y.
Pittman CU.
Synthesis
2010,
1209
30 Ye G.
Zhou A.
Henry WP.
Song Y.
Chatterjee S.
Beard DJ.
Pittman CU.
J.
Org. Chem.
2008,
73:
5170
31 Chatterjee S.
Ye G.
Pittman CU.
Tetrahedron
Lett.
2010,
51:
1139
32 Ciurdaru G.
Ciuciu M.
J. Prakt. Chem.
1979,
321:
320
33 Coppinger GM.
J.
Am. Chem. Soc.
1954,
76:
1372
34 Ruske W.
Keilert M.
Chem. Ber.
1961,
94:
2695
35 Rattananakin P.
Pittman CU.
Collier WE.
Saebo S.
Struct.
Chem.
2007,
18:
399
36 Shibata Y, Aoyagi K, Takahashi H, Iwasa T, and Take T. inventors; PCT.
Int. Appl. WO2000017174.
; Chem. Abstr. 2000 , 132,
251145
37 CCDC 765577 (3d ),
765578 (4d ), and 765826 (9a )
contain the supplementary crystallographic data for this paper. These
data can be obtained free of charge from The Cambridge Crystallographic
Data Centre via www.ccdc.cam.ac.uk/data_request/cif.
