Abstract
Three new pyridyl thienopyridines, 5-pyridin-2-yl-thieno[3,2-b ]pyridine, 6-pyridin-2-yl-thieno[2,3-b ]pyridine and 6-pyridin-2-yl-thieno[3,2-c ]pyridine, have been synthesized, each through a different synthetic sequence. Overall
yields ranged from 8% to 32%.
Key words
ring closure - fused-ring systems - heterocycles - pyridines - conjugation
References
<A NAME="RT12905SS-1">1 </A>
Constable EC.
Dunne SJ.
Rees DGF.
Schmitt CX.
Chem. Commun.
1996,
1169
<A NAME="RT12905SS-2">2 </A>
Dunne SJ.
Constable EC.
Inorg. Chem. Commun.
1998,
1:
167
<A NAME="RT12905SS-3">3 </A>
Amr A.-GE.
Hegab MI.
Ibraheim AA.
Abdulla MM.
Monatsh. Chem.
2003,
134:
1395
<A NAME="RT12905SS-4">4 </A>
Goerlitzer K.
Kramer C.
Pharmazie
2000,
55:
645
<A NAME="RT12905SS-5">5 </A>
Halverson AP.
J. Heterocycl. Chem.
1996,
727
<A NAME="RT12905SS-6">6 </A>
Zhang QT.
Tour JM.
J. Am. Chem. Soc.
1997,
119:
9624
<A NAME="RT12905SS-7">7 </A>
Raich WJ.
Hamilton CS.
J. Am. Chem. Soc.
1957,
79:
3800
<A NAME="RT12905SS-8">8 </A>
Fukumi H.
Sugiyama M.
Sakamoto T.
Chem. Pharm. Bull.
1989,
37:
1197
<A NAME="RT12905SS-9">9 </A>
Sugiyama M.
Sakamoto T.
Tabata K.
Fukumi H.
Chem. Pharm. Bull.
1989,
37:
2717
<A NAME="RT12905SS-10">10 </A>
Barker JM.
Huddleston PR.
Needs PW.
J. Chem. Res., Miniprint
1989,
351
<A NAME="RT12905SS-11">11 </A>
Sugiyama M.
Sakamoto T.
Tabata K.
Endo K.
Ito K.
Chem. Pharm. Bull.
1989,
37:
2091
<A NAME="RT12905SS-12">12 </A>
Conde S.
Corral C.
Lissavetzky J.
J. Heterocycl. Chem.
1985,
22:
301
<A NAME="RT12905SS-13">13 </A>
Meth-Cohn O.
Narine B.
Synthesis
1980,
133
<A NAME="RT12905SS-14">14 </A>
Yadav JS.
Reddy BVS.
Madhavi AV.
Ganesh YSS.
J. Chem. Res.
2002,
5:
236
<A NAME="RT12905SS-15">15 </A>
Cymmerman-Craig J.
Naik AR.
J. Am. Chem. Soc.
1962,
84:
3410
<A NAME="RT12905SS-16">16 </A>
Donaruma LG.
Heldt WZ.
Org. React. (N.Y.)
1960,
11:
1
<A NAME="RT12905SS-17">17 </A>
Gawley RE.
Org. React. (N.Y.)
1988,
35:
1
<A NAME="RT12905SS-18">18 </A>
Meth-Cohn O.
Narine B.
Tarnowski B.
J. Chem. Soc., Perkin Trans. 1
1981,
1531
<A NAME="RT12905SS-19">19 </A>
Meth-Cohn O.
Stanforth P. In Comprehensive Organic Synthesis, Vol. 2
Trost BM.
Fleming I.
Pergamon Press;
Oxford:
1991.
p.777
<A NAME="RT12905SS-20">20 </A>
Fang Y.-Q.
Hanan GS.
Synlett
2003,
852
<A NAME="RT12905SS-21">21 </A>
Negishi E.
King AO.
Okukado N.
J. Org. Chem.
1977,
42:
1821
<A NAME="RT12905SS-22">22 </A>
Knochel P.
Singer RD.
Chem. Rev.
1993,
93:
2117
<A NAME="RT12905SS-23">23 </A>
Miller JA.
Farrell RP.
Tetrahedron Lett.
1998,
39:
6441
<A NAME="RT12905SS-24">24 </A>
Meth-Cohn O.
Narine B.
Tetrahedron Lett.
1978,
2045
<A NAME="RT12905SS-25">25 </A>
Meth-Cohn O.
Narine B.
Tarnowski B.
Hayes R.
Keyzad A.
J. Chem. Soc., Perkin Trans. 1
1981,
2509
<A NAME="RT12905SS-26">26 </A>
Klemm LH.
Hartling R.
J. Heterocycl. Chem.
1976,
13:
1197
<A NAME="RT12905SS-27">27 </A>
Klemm LH.
Bajer M.
J. Heterocycl. Chem.
1979,
16:
1289
<A NAME="RT12905SS-28">28 </A>
Barker JM.
Huddleston PR.
Holmes D.
J. Chem. Res., Miniprint
1985,
7:
2501
<A NAME="RT12905SS-29">29 </A>
Gronowitz S.
Gestblom B.
Mathiasson B.
Ark. Kemi
1963,
20:
407
<A NAME="RT12905SS-30">30 </A>
Hibino S.
Kano S.
Mochizuki N.
Sugino E.
J. Org. Chem.
1984,
49:
5006
<A NAME="RT12905SS-31">31 </A>
Sugimoto H.
Kuramoto K.
Inoue S.
J. Chem. Soc., Perkin Trans. 1
2002,
15:
1826
<A NAME="RT12905SS-32">32 </A>
Carsky P.
Huenig S.
Stemmler I.
Scheutzow D.
Liebigs Ann. Chem.
1980,
2:
291
<A NAME="RT12905SS-33">33 </A>
Furniss BS.
Hannaford AJ.
Smith PWG.
Tatchell AR.
Vogel’s Textbook of Practical Organic Chemistry , 5th ed.
Longman Scientific & Technical;
Essex:
1989.
p.498