Abstract
A synthesis of haloisoquinolines through electrophilic cyclisation involving an electrophilic-exchange process has been developed. A variety of 2-alkynyl benzyl azides are cyclised in the presence of KX (X = I, Br, Cl) and electrophilic fluoride reagents, to afford the corresponding haloisoquinolines in moderate to good yields. Reagents for electrophilic halogenation have been generated from their inorganic salts (M+X-) by oxidation with a Selectfluor reagent and reacted in situ with the substrates.
Keywords
References
1.
Tan B.
,
Shi Z.
,
Chua P.J.
, and
Zhong G.
, Org. Lett. , 2008 , 10 , 3425 .
2.
Huo Z.
,
Gridnev I.D.
, and
Yamamoto Y.
, J. Org. Chem. , 2010 , 75 , 1266 .
3.
Yu X.
, and
Wu J.
, J. Comb. Chem. , 2009 , 11 , 895 .
4.
Ye S.
,
Wang H.
, and
Wu J.
, ACS Comb. Sci. , 2011 , 13 , 120 .
5.
Ouyang H.-C.
,
Tang R.-Y.
,
Zhong P.
,
Zhang X.-G.
, and
Li J.-H.
, J. Org. Chem. , 2011 , 76 , 223 .
6.
Tanner D.D.
,
Rowe J.E.
, and
Potter A.
, J. Org. Chem. , 1986 , 51 , 457 .
7.
Breslow R.
,
Corcoran R.J.
,
Snider B.B.
,
Doll R.J.
,
Khanna P.L.
, and
Kaleya R.
J. Am. Chem. Soc. , 1977 , 99 , 905 .
8.
Ben-Valid S.
,
Quntar A.A.A.
, and
Srebnik M.
, J. Org. Chem. , 2005 , 70 , 3554 .
9.
Manarin F.
,
Roehrs J.A.
,
Gay R.M.
,
Brandão R.
,
Menezes P.H.
,
Nogueira C.W.
, and
Zeni G.
, J. Org. Chem. , 2009 , 74 , 2153 .
10.
Godoi B.
,
Sperança A.
,
Back D.F.
,
Brandão R.
,
Nogueira C.W.
, and
Zeni G.
, J. Org. Chem. , 2009 , 74 , 3469 .
11.
Zhang W.
,
Zheng S.
,
Liu N.
,
Werness J.B.
,
Guzei I.A.
, and
Tang W.
, J. Am. Chem. Soc. , 2010 , 132 , 3664 .
12.
Brabandt W.V.
, and
Kimpe N.D.
, J. Org. Chem. , 2005 , 70 , 8717 .
13.
Verhelst T.
,
Verbeeck S.
,
Ryabtsova O.
,
Depraetere S.
, and
Maes B.U.W.
, Org. Lett. , 2011 , 13 , 272 .
14.
Manarin F.
,
Roehrs J.A.
,
Gay R.M.
,
Brandão R.
,
Menezes P.H.
,
Nogueira C.W.
, and
Zeni G.
J. Org. Chem. , 2009 , 74 , 2153 .
15.
Syvret R.G.
,
Butt K.M.
,
Nguyen T.P.
,
Bulleck V.L.
, and
Rieth R.D.
, J. Org. Chem. , 2002 , 67 , 4487 .
16.
Ztspan M.
,
Iskra J.
, and
Stavber S.
, Tetrahedron Lett. , 1997 , 38 , 6305 .
17.
Zhang H.-P.
,
Yu S.-C.
,
Liang Y.
,
Peng P.
,
Tang B.-X.
, and
Li J.-H.
, Synlett , 2011 , 7 , 982 .
18.
Tang B.-X.
,
Yin Q.
,
Tang R.-Y.
, and
Li J.-H.
, J. Org. Chem. , 2008 , 73 , 9008 .
19.
Huang Q.
,
Hunter J.A.
, and
Larock R.C.
, J. Org. Chem. , 2002 , 67 , 3437 .
20.
Zhang H.-P.
,
Li H.-Y.
, and
Xiao H.-F.
, J. Chem. Res. , 2013 , 37 , 556 .
21.
Chowdhury C.
,
Mandal S.B.
, and
Achari B.
, Tetrahedron Lett. , 2005 , 46 , 8531 .
