Abstract
The photochemical formation is described of N-arylacetyl lactams from the corresponding N-phenylglyoxylic acid derivatives of pyrrolidine and piperidine-2-carboxylic acids in an acetone:water mixture containing potassium carbonate. Evidence is presented for the possible formation and cleavage of a cyclic ether during this process which leads to the 1, 4-transfer of a carbonyl group.
References
1.
Konomi
T.
, and
Tani
H.
, J. Polym. Sci. , Part A, 1969 , 7 , 2255 .
2.
Ishida
A.
, and
Mukaiyama
T.
, Bull. Chem. Soc. Jpn , 1978 , 51 , 2077 .
3.
Li
C.Y.
,
Tsai
W.
,
Damu
A.G.
,
Lee
E.J.
,
Wu
T.S.
,
Dung
N.X.
,
Thang
T.D.
, and
Thanh
L.
, J. Agric. Food Chem. , 2007 , 55 , 9436 .
4.
Sasaki
H.
,
Mori
Y.
,
Nakamura
J.
, and
Shibasaki
J.
, J. Med. Chem. , 1991 , 34 , 628 .
5.
Akihiko
I.
,
Takashi
B.
, and
Teruaki
M.
, Chem. Lett. , 1976 , 7 , 711 .
6.
Fuks
R.
, and
Viehe
H.G.
, Tetrahehron , 1969 , 25 , 5721 .
7.
Pagadala
R.
,
Meshram
J.S.
,
Chopde
H.N.
,
Jetti
V.
, and
Udayini
V.
J. Heterocyclic Chem. , 2011 , 48 , 1067 .
8.
Zhang
J.
, and
Hong
S.H.
, Org. Lett. , 2012 , 14 , 4646 .
9.
Wang
R.T.
,
Chen
C.F.
,
Duesler
E.
, and
Mariano
P.S.
, J. Org. Chem. , 2004 , 69 , 1215 .
10.
Akermark
B.
,
Johansson
N.G.
, and
Sjoberg
B.
, Tetrahehron Lett. , 1969 , 5 , 371 .
11.
Griesbeck
A.G.
, and
Heckroth
H.K.
, Synlett. , 2002 , 1 , 131 .
12.
Jesuraj
J.L.
, and
Sivaguru
J.
, Chem. Commun. , 2010 , 46 , 4791 .
13.
Li
K.T.
,
Lin
Y.B.
, and
Yang
D.Y.
, Org. Lett. , 2012 , 14 , 1190 .
14.
Bentrude
W.G.
, and
Darnall
K.R.
, Chem. Commun. , 1969 , 15 , 862 .
15.
Goka
T.
,
Shizoka
H.
, and
Matsui
K.
, J. Org. Chem. , 1978 , 43 , 1361 .
16.
Maeda
S.
,
Ohno
K.
, and
Morokuma
K.
, J. Phys. Chem. Lett. , 2010 , 1 , 1841 .
17.
Dalton
J.C.
,
Wriede
P.A.
, and
Turro
N.J.
, J. Am. Chem. Soc. , 1970 , 92 , 1318 .
18.
Dalton
J.C.
, and
Tremont
S.J.
, J. Am. Chem. Soc. , 1975 , 97 , 6916 .
19.
Yarchak
M.L.
,
Dalton
J.C.
, and
Saunders
W.H.
, J. Am. Chem. Soc. , 1973 , 95 , 5228 .
20.
Cai
X.C.
,
Yamaji
M.
,
Sakamoto
M.
,
Fujitsuka
M.
, and
Majima
T.
, Chem. Phys. Lett. , 2007 , 443 , 248 .
21.
Cooper
A.J.L.
,
Ginos
J.Z.
, and
Meister
A.
, Chem. Rev. , 1983 , 83 , 321 .
22.
Cayley
A.N.
,
Gallagher
K.A.
,
Menard
M.C.
,
Schmidt
J.P.
,
Diorazio
L.J.
, and
Taylor
R.J.K.
, Synthesis , 2008 , 23 , 384 .