Abstract
An efficient selectfluor-mediated cyclisation of 2-arylethynyl-benzyl azides at 80 °C in MeCN yielded 12 arylated triazolo-isoindoline derivatives (seven of which are novel). Products bearing either electron-donating or electron-withdrawing groups on the aromatic ring were formed in comparable yields.
References
1.
Tam
A.
,
Arnold
U.
,
Soellner
M. B.
, and
Raines
R. T.
, J. Am. Chem. Soc. , 2007 , 129 , 12670 .
2.
Buckle
D.R.
,
Rockell
C. J. M.
,
Smith
H.
, and
Spicer
B. A.
, J. Med. Chem. , 1986 , 29 , 2262 .
3.
Tatsuta
K.
,
Ikeda
Y.
, and
Miura
S.
, J. Antibiot. , 1996 , 49 , 836 .
4.
Chowdhury
C.
,
Mandal
S. B.
, and
Achari
B.
, Tetrahedron Lett. , 2005 , 46 , 8531 .
5.
Shafran
E.A.
,
Bakulev
V. A.
,
Rozin
Y. A.
, and
Shafran
Y. M.
, Chem. Heterocycl. Compd. , 2008 , 44 , 1040 .
6.
Arnanz
A.
,
Pintado-Sierra
M.
,
Corma
A.
,
Iglesias
M.
, and
Sanchez
F.
, Adv. Synth. Catal. , 2012 , 354 , 1347 .
7.
Rossy
C.
,
Majimel
J.
,
Delapierre
M. T.
,
Fouquet
E.
, and
Felpin
F.-X.
, J. Organometallic Chem. , 2014 , 755 , 78 .
8.
Orski
S.V.
,
Sheppard
G. R.
,
Arumugam
S.
,
Arnold
R. M.
,
Popik
V. V.
, and
Locklin
J.
, Langmuir , 2012 , 28 , 14693 .
9.
Laali
K.K.
,
Nandi
G. C.
, and
Bunge
S. D.
, Tetrahedron Lett. , 2014 , 55 , 2401 .
10.
Zhang
H.-P.
, and
Li
H.-Y.
, J. Chem. Res. , 2014 , 38 , 682 .
11.
Rajawinslin
R.R.
,
Raihan
M. J.
,
Janreddy
D.
,
Kavala
V.
,
Kuo
C.-W.
,
Kuo
T.-S.
,
Chen
M.-L.
,
He
C.-H.
, and
Yao
C.-F.
, Tetrahedron , 2014 , 70 , 7505 .
12.
Fiandanese
V.
,
Marchese
G.
,
Punzi
A.
,
Iannone
F.
, and
Rafaschieri
G. G.
, Tetrahedron , 2010 , 66 , 8846 .
13.
Banday
A.
, and
Hrubya
V. J.
, Synlett , 2014 , 25 , 2463 .
14.
Brahma
K.
,
Achari
B.
, and
Chowdhury
C.
, Synthesis , 2013 , 45 , 545 .