Abstract
2-Alkynyl benzyl azides smoothly underwent an electrocyclic reaction catalysed by palladium to selectively afford either 4-bromoisoquinoline and 4-bromoisquinolones under different conditions. 4-Bromoisoquinoline was synthesised in the presence of PdBr2/CuBr2/LiBr in MeCN, and 4-bromoisoquinolone was selectively produced with PdBr2/CuBr2/HOAc in CH2ClCH2Cl. A bromine was introduced into the products which makes the methodology more attractive for organic synthesis.
References
1.
Bentley K.W.
, Nat. Prod. Rep. , 2005 , 22 , 249 .
2.
Bentley K.W.
, Nat. Prod. Rep. , 2006 , 23 , 444 .
3.
Delcey M.C.
,
Croisy A.
,
Carrez D.
,
Huel C.
,
Chiaroni A.
,
Ducrot P.
,
Bisagni E.
,
Jin L.
, and
Leclercq G.
, Bioorg. Med. Chem. , 2000 , 8 , 2629 .
4.
Jayaraman M.
,
Fox B.M.
,
Hollingshead M.
,
Kohlhagen G.
,
Pommier Y.
, and
Cushman M.
, J. Med. Chem. , 2000 , 43 , 3688 .
5.
Zhang H.
,
Zembower D.
, and
Chen Z.
Bioorg. Med. Chem. Lett. , 1997 , 7 , 2687 .
6.
Bernan V.S.
,
Montenegro D.A.
,
Korshalla J.D.
,
Maiese W.M.
,
Steinberg D.A.
, and
Greenstein M.J.
, Antibiotics , 1994 , 47 , 1417 .
7.
Li S.W.
,
Nair M.G.
,
Edwards D.M.
,
Kisluick R.L.
,
Gaument Y.
,
Dev I.K.
,
Duch D.S.
,
Humphreys J.
,
Smith G.K.
, and
Ferone R.
, J. Med. Chem. , 1991 , 34 , 2746 .
8.
Huang Q.
,
Hunter J.A.
, and
Larock R.C.
, Org. Lett. , 2001 , 3 , 2973 .
9.
Korivi R.P.
,
Wu W.-J.
, and
Cheng C.-H.
, Chem., Eur. J. , 2009 , 15 , 10727 .
10.
Korivi R.P.
,
Wu W.-J.
, and
Cheng C.-H.
, Chem., Eur. J. , 2010 , 16 , 282 .
11.
Chinnagolla R.K.
,
Pimparkar S.
, and
Jeganmohan M.
, Org. Lett. , 2012 , 14 , 3032 .
12.
Jagtap P.G.
,
Baloglu E.
,
Southan G.
,
Williams W.
,
Roy A.
,
Nivorozhkin A.
,
Landrau N.
,
Desisto K.
,
Salzman A.L.
, and
Szabo C.
, Org. Lett. , 2005 , 7 , 1753 .
13.
Fisher L.E.
,
Muchowski J.M.
, and
Clark R.D.
, J. Org. Chem. , 1992 , 57 , 2700 .
14.
Bischler A.
, and
Napieralski B.
, Ber. Dtsch. Chem. Ges. , 1893 , 26 , 1903 .
15.
Pictet A.
, and
Spengler T.
, Ber. Dtsch. Chem. Ges. , 1911 , 44 , 2030 .
16.
Bergstrom F.W.
, Chem. Rev. , 1944 , 35 , 77 .
17.
Korivi R.P.
, and
Cheng C.-H.
, Org. Lett. , 2005 , 7 , 5179 .
18.
Bajracharya G.B.
,
Pahadi N.K.
,
Gridnev I.D.
, and
Yamamoto Y.
, J. Org. Chem. , 2006 , 71 , 6204 .
19.
Niu Y.-N.
,
Yan Z.-Y.
,
Gao G.-L.
,
Wang H.-L.
,
Shu X.-Z.
,
Ji K.-G.
, and
Liang Y.-M.
, J. Org. Chem. , 2009 , 74 , 2893 .
20.
Lim S.-G.
,
Lee J.H.
,
Moon C.W.
,
Hong J.-B.
, and
Jun C.-H.
, Org. Lett. , 2003 , 5 , 2759 .
21.
Guimond N.
, and
Fagnou K.
, J. Am. Chem. Soc. , 2009 , 131 , 12050 .
22.
Wang B.
,
Lu B.
,
Jiang Y.
,
Zhang Y.
, and
Ma D.
, Org. Lett. , 2008 , 10 , 2761 .
23.
Huo Z.
, and
Yamamoto Y.
, Tetrahedron Lett. , 2009 , 50 , 3651 .
24.
Ramakrishna T.V.V.
, and
Sharp P.R.
, Org. Lett. , 2003 , 5 , 877 .
25.
Pellegatti L.
,
Vedrenne E.
,
Hiebel M.-A.
,
Buron F.
,
Massip S.
,
Leger J.-M.
,
Jarry C.
, and
Routier S.
, Tetrahedron Lett. , 2011 , 52 , 5224 .
26.
Guchhait S.K.
, and
Madaan C.
, Org. Biomol. Chem. , 2010 , 8 , 3631 .
27.
Mert-Balci F.
,
Conrad J.
,
Meindl K.
,
Schulz T.
,
Stalke D.
, and
Beifuss U.
, Synthesis , 2008 , 22 , 3649 .
28.
Antczak M.I.
, and
Ready J.M.
, Chem. Sci. , 2012 , 3 , 1450 .
29.
Tyagi V.
,
Khan S.
,
Giri A.
,
Gauniyal H.M.
,
Sridhar B.
, and
Chauhan P.M.S.
, Org. Lett. , 2012 , 14 , 3126 .
30.
Boissarie P.J.
,
Hamilton Z.E.
,
Lang S.
,
Murphy J.A.
, and
Suckling C.J.
, Org. Lett. , 2011 , 13 , 6256 .
31.
Vlaar T.
,
Ruijter E.
,
Znabet A.
,
Janssen E.
,
de Kanter F.J.J.
,
Bert U.W.
,
Maes B.U.
, and
Orru R.V.A.
, Org. Lett. , 2011 , 13 , 6496 .
32.
Qiu G.
,
He Y.
, and
Wu J.
, Chem. Commun. , 2012 , 48 , 3836 .
33.
Zhang H.-P.
,
Yu S.-C.
,
Liang Y.
,
Peng P.
,
Tang B.-X.
, and
Li J.-H.
, Synlett , 2011 , 0982 .
34.
Zhang H.-P.
,
Yang X.-H.
,
Peng P.
, and
Li J.-H.
, Synthesis , 2011 , 1219 .
35.
Fischer D.
,
Tomeba H.
,
Pahadi N.K.
,
Patil N.T.
, and
Yamamoto Y.
, Angew. Chem. Int. Ed. , 2007 , 46 , 4764 .
36.
Yu X.
, and
Wu J.
, J. Comb. Chem. , 2009 , 11 , 895 .
37.
Usifoh C.O.
, J. Heterocycl. Chem. , 2001 , 38 , 597 .
