Abstract
A good yield in the synthesis of dimethyl 2-{1-[(1-methylimidazol-2-yl)sulfanyl]-1H-isoquinolin-2-yl}but-2-enedioate and related compounds is described involving the reaction of acetylenic esters and 1-methylimidazole-5-thiol or 1-methyltetrazole-5-thiol as SH-acids in the presence of isoquinoline. This one-pot method is simple and effective under mild conditions.
References
1.
Scott J.D.
, and
Williams R. M.
, Chem. Rev. , 2002 , 102 , 1669 .
2.
Sorgi K.L.
,
Maryanoff C. A.
,
McComsey D. F.
,
Graden D. W.
, and
Maryanoff B. E.
, J. Am. Chem. Soc. , 1990 , 112 , 3567 .
3.
Lukevics E.
,
Segal I.
,
Zablotskaya A.
, and
Germane S.
, Molecules , 1997 , 2 , 180 .
4.
Knölker H.-J.
, and
Agarwal S.
, Tetrahedron Lett. , 2005 , 46 , 1173 .
5.
Yadav J.S.
,
Reddy B. V. S.
,
Yadav N. N.
, and
Gupta M. K.
, Tetrahedron Lett. , 2008 , 49 , 2815 .
6.
Nassiri M.
,
Maghsoodlou M. T.
,
Heydari R.
, and
Khorassani S. M. H.
, Mol. Divers. , 2008 , 12 , 111 .
7.
Yavari I.
,
Ghazanfarpour-Darjani M.
,
Sabbaghan M.
, and
Hossaini Z.
, Tetrahedron Lett. , 2007 , 48 , 3749 .
8.
Yadav J.S.
,
Reddy B. V. S.
,
Yadav N. N.
,
Gupta M. K.
, and
Sridhar B.
, J. Org. Chem. , 2008 , 73 , 6857 .
9.
Shaabani A.
,
Rezayan A. H.
,
Sarvary A.
,
Heidary M.
, and
Weng N. S.
, Tetrahedron , 2009 , 65 , 6063 .
10.
Xia E.Y.
,
Sun J.
,
Yao R.
, and
Yan C. G.
, Tetrahedron , 2010 , 66 , 3569 .
11.
Anary-Abbasinejad M.
,
Anaraki-Ardakani H.
,
Mosslemina M. H.
, and
Khavasi H. R.
, J. Braz. Chem. Soc. , 2010 , 21 , 319 .
12.
Yavari I.
,
Piltan M.
, and
Moradi L.
, Tetrahedron , 2009 , 65 , 2067 .
13.
Khaleghi F.
,
Din L. B.
,
Jantan I.
,
Yaacob W. A.
, and
Khalilzadeh M. A.
, Tetrahedron Lett. , 2011 , 52 , 7182 .
14.
Niknam N.
, and
Hassanabadi A.
, J. Chem. Res. , 2014 , 38 , 662 .
15.
Hassanabadi A.
, and
Zhiani R.
, J. Chem. Res. , 2014 , 38 , 247 .
16.
Anary-Abbasinejad M.
,
Mosslemin M. H.
,
Hassanabadi A.
, and
Tabatabaee M.
, Synth. Commun. , 2008 , 38 , 3700 .
17.
Anary-Abbasinejad M.
,
Poorhassan E.
, and
Hassanabadi A.
, Synlett , 2009 , 1929 .
18.
Acheson R.M.
, and
Elmore N. F.
, Adv. Heterocycl. Chem. , 1978 , 23 , 263 .
19.
Acheson R.M.
, and
Woollard J.
, J. Chem. Soc., Perkin Trans 1 , 1975 , 438 .
20.
Acheson R.M.
, and
Taylor G. A.
, J. Chem. Soc. , 1960 , 1691 .
21.
Yavari I.
,
Anary-Abbasinejad M.
, and
Hossaini Z.
, Pol. J. Chem. , 2004 , 78 , 361 .
22.
Huisgen R.
, and
Herbig K.
, Liebigs Ann. Chem. , 1965 , 688 , 98 .
23.
Huisgen R.
,
Morikawa M.
,
Herbig K.
, and
Brunn E.
, Chem. Ber. , 1967 , 100 , 1094 .
24.
Winterfeldt E.
, Chem. Ber. , 1965 , 98 , 3537 .
25.
Nair V.
,
Rajesh C.
,
Vinod A. U.
,
Bindu S.
,
Sreekanth A. R.
,
Mathen J. S.
, and
Balagopal L.
, Acc. Chem. Res. , 2003 , 36 , 899 .