Abstract
Benzopyran-annulated thiopyrano[2,3-b]thiochromen-5(4H)-ones have been synthesized by the
domino Knoevenagel-hetero-Diels-Alder (DKHDA)
reaction of 4-hydroxydithiocoumarin with O-allylated salicylaldehyde
and O-propargylated salicylaldehyde in aqueous medium.
The reaction requires only a single step operation and is highly
regio- and stereoselective providing potentially bioactive polycyclic
heterocycles in high yields.
Key words
aqueous medium - domino Knoevenagel-hetero-Diels-Alder
reaction - stereoselective - regioselective - 4-hydroxydithiocoumarin
References
<A NAME="RZ20110SS-1">1</A>
Anastas PT.
Warner JC.
Green
Chemistry, Theory and Practice
Oxford University
Press;
Oxford:
1998.
<A NAME="RZ20110SS-2A">2a</A>
Ramachary DB.
Kishor M.
J.
Org. Chem.
2007,
72:
5056
<A NAME="RZ20110SS-2B">2b</A>
Leitner W.
Green
Chem.
2009,
11:
603
<A NAME="RZ20110SS-3A">3a</A>
Toda F.
Tanaka K.
Chem.
Rev.
2000,
100:
1025
<A NAME="RZ20110SS-3B">3b</A>
Varma RS.
Green Chem.
1999,
1:
43
<A NAME="RZ20110SS-4">4</A>
Polshettiwar V.
Varma RS.
Chem. Soc. Rev.
2008,
37:
1546
<A NAME="RZ20110SS-5A">5a</A>
Lindstrom UM.
Chem. Rev.
2002,
102:
2751
<A NAME="RZ20110SS-5B">5b</A>
Li C.-J.
Chem.
Rev.
2005,
105:
3095
<A NAME="RZ20110SS-5C">5c</A>
Sharma G.
Kumar R.
Chakraborti AK.
Tetrahedron
Lett.
2008,
49:
4269
<A NAME="RZ20110SS-5D">5d</A>
Ranu BC.
Banerjee S.
Tetrahedron
Lett.
2007,
48:
141
<A NAME="RZ20110SS-6">6</A>
Sheldon RA.
Chem.
Commun.
2001,
2399
<A NAME="RZ20110SS-7A">7a</A>
Luo ZY.
Zang QS.
Oderaotoshi Y.
Curran DP.
Science
2001,
291:
1766
<A NAME="RZ20110SS-7B">7b</A>
Harvath IT.
Acc. Chem. Res.
1998,
31:
641
<A NAME="RZ20110SS-8">8</A>
Oakes RS.
Califford AA.
Rayner CM.
J. Chem. Soc., Perkin Trans. 1
2001,
917
<A NAME="RZ20110SS-9A">9a</A>
Kumar D.
Patel G.
Mishra BG.
Varma RS.
Tetrahedron
Lett.
2008,
49:
6974
<A NAME="RZ20110SS-9B">9b</A>
Chen J.
Spear SK.
Huddleston JG.
Rogers RD.
Green
Chem.
2005,
7:
64
<A NAME="RZ20110SS-9C">9c</A>
Kumar R.
Chaudhary P.
Nimesh S.
Chandra R.
Green Chem.
2006,
8:
356
<A NAME="RZ20110SS-10A">10a</A>
Liu S.
Xiao J.
J.
Mol. Catal. A: Chem.
2007,
270:
1
<A NAME="RZ20110SS-10B">10b</A>
Sheldon AR.
Green Chem.
2005,
7:
267
<A NAME="RZ20110SS-10C">10c</A>
Alonso F.
Beletskaya IP.
Yus M.
Tetrahedron
2008,
64:
3047
<A NAME="RZ20110SS-10D">10d</A>
Horvath IT.
Green Chem.
2008,
10:
1024
<A NAME="RZ20110SS-11A">11a</A>
Organic Synthesis in Water
Grieco PA.
Blacky Academic & Professonal
Publishers;
London:
1998.
p.82
<A NAME="RZ20110SS-11B">11b</A>
Comprehensive
Organic Reactions in Aqueous Media
Li C.-J.
Chan T.-H.
Wiley;
New
York:
2007.
<A NAME="RZ20110SS-11C">11c</A>
Shaughnessy KH.
Devasher RB.
Curr.
Org. Chem.
2005,
9:
585
<A NAME="RZ20110SS-12A">12a</A>
Yadav JS.
Reddy BVS.
Sadashiv K.
Padmavani B.
Adv. Synth. Catal.
2004,
346:
607
<A NAME="RZ20110SS-12B">12b</A>
Yamanaka M.
Nishida A.
Nakagana M.
Org.
Lett.
2000,
2:
159
<A NAME="RZ20110SS-12C">12c</A>
Deligny M.
Carreaux F.
Toupet L.
Carboni B.
Adv. Synth. Catal.
2003,
345:
1215
<A NAME="RZ20110SS-12D">12d</A>
Berkessel A.
Erturk E.
Laporte C.
Adv.
Synth. Catal.
2006,
348:
223
<A NAME="RZ20110SS-12E">12e</A>
Baudelle R.
Melnyk P.
Deprez B.
Tartar A.
Tetrahedron
1998,
54:
4125
<A NAME="RZ20110SS-13A">13a</A>
Tietze LF.
Chem. Rev.
1996,
96:
115
<A NAME="RZ20110SS-13B">13b</A>
Tietze LF.
Brasche G.
Gericke K.
Domino Reactions in Organic Synthesis
Wiley-VCH;
Weinheim:
2006.
<A NAME="RZ20110SS-13C">13c</A>
Tietze LF.
Rackelmann N.
Pure
Appl. Chem.
2004,
76:
1967
<A NAME="RZ20110SS-13D">13d</A>
Tietze LF.
Ott C.
Gerke K.
Buback M.
Angew. Chem., Int. Ed. Engl.
1993,
32:
1485
<A NAME="RZ20110SS-14A">14a</A>
Majumdar KC.
Taher A.
Ray K.
Tetrahedron Lett.
2009,
50:
3889
<A NAME="RZ20110SS-14B">14b</A>
Ramesh E.
Raghunathan R.
Tetrahedron Lett.
2008,
49:
1812
<A NAME="RZ20110SS-14C">14c</A>
Lee YR.
Xia L.
Tetrahedron
Lett.
2008,
49:
3283
<A NAME="RZ20110SS-14D">14d</A>
Jimenez-Alonso S.
Chavez H.
Estevez-Braun A.
Ravelo AG.
Feresin G.
Tapia A.
Tetrahedron
2008,
64:
8938
<A NAME="RZ20110SS-14E">14e</A>
Lee YR.
Kim YM.
Kim SH.
Tetrahedron
2009,
65:
101
<A NAME="RZ20110SS-14F">14f</A>
Majumdar KC.
Taher A.
Ponra S.
Tetrahedron
Lett.
2010,
51:
147
<A NAME="RZ20110SS-14G">14g</A>
Majumdar KC.
Taher A.
Ponra S.
Tetrahedron
Lett.
2010,
51:
2297
<A NAME="RZ20110SS-14H">14h</A>
Khoshkholgh MJ.
Balalaie S.
Bijanzadeh HR.
Gross JH.
Synlett
2009,
55
<A NAME="RZ20110SS-14I">14i</A>
Khoshkholgh MJ.
Balalaie S.
Bijanzadeh HR.
Gross JH.
ARKIVOC
2009,
(ix):
114
<A NAME="RZ20110SS-14J">14j</A>
Khoshkholgh MJ.
Balalaie S.
Bijanzadeh HR.
Rominger F.
Gross JH.
Tetrahedron Lett.
2008,
49:
6965
<A NAME="RZ20110SS-14K">14k</A>
Khoshkholgh MJ.
Lotfi M.
Balalaie S.
Rominger F.
Tetrahedron
2009,
65:
4228
<A NAME="RZ20110SS-15A">15a</A>
Majumdar KC.
Alam S.
J.
Chem. Res.
2006,
281
<A NAME="RZ20110SS-15B">15b</A>
Majumdar KC.
Alam S.
Org. Lett.
2006,
8:
4059
<A NAME="RZ20110SS-15C">15c</A>
Majumdar KC.
Bandyopadhyay A.
Biswas A.
Tetrahedron
2003,
59:
5289
<A NAME="RZ20110SS-16A">16a</A>
Vink P. inventors; Dutch Patent 6
411 477.
;
Chem. Abstr., 1965, 63,
13265
<A NAME="RZ20110SS-16B">16b</A>
El-Subbagh HI.
El-Emam AA.
El-Ashmawy MB.
Shehata IA.
Arch.
Pharm. Res.
1990,
13:
24 ;
and references cited therein
<A NAME="RZ20110SS-17A">17a</A>
Korkina GL.
Afanas’ev IB.
Adv. Pharmacol.
1997,
38:
151
<A NAME="RZ20110SS-17B">17b</A>
Buslig BS. In Flavonoids in Living
Systems: Advances in Experimental Medicine and Biology
Vol.
439:
Manthy JA.
Plenum;
New
York:
1998.
<A NAME="RZ20110SS-17C">17c</A>
Organic Chemical
Drugs and their Synonyms
7th ed.:
Negwer M.
Akademie;
Stuttgart:
1994.
<A NAME="RZ20110SS-17D">17d</A>
Groundwater PW.
Solomon KRH.
Drewe JA.
Munawar MA. In Progress in Medicinal
Chemistry
Vol. 33:
Ellis GP.
Luscombe DK.
Elsevier;
Amsterdam:
1996.
p.233
<A NAME="RZ20110SS-18A">18a</A>
Majumdar KC.
Khan AT.
Saha S.
Synlett
1991,
595
<A NAME="RZ20110SS-18B">18b</A>
Majumdar KC.
Bandyopadhyay A.
Ghosh SK.
Synth. Commun.
2004,
34:
2159
<A NAME="RZ20110SS-18C">18c</A>
Majumdar KC.
Bandyopadhyay A.
Monatsh.
Chem.
2004,
135:
581
<A NAME="RZ20110SS-18D">18d</A>
Majumdar KC.
Saha S.
Khan AT.
Indian J. Chem., Sect. B: Org. Chem. Incl.
Med. Chem.
1994,
33:
216
<A NAME="RZ20110SS-19A">19a</A>
Majumdar KC.
Khan AT.
Saha S.
Synth. Commun.
1992,
22:
901
<A NAME="RZ20110SS-19B">19b</A>
Majumdar KC.
Bandyopadhyay A.
Biswas A.
Tetrahedron
2003,
59:
5289
<A NAME="RZ20110SS-20">20</A>
Gazith M.
Noys RM.
J. Am. Chem. Soc.
1955,
77:
6091
<A NAME="RZ20110SS-21">21</A>
Bashiardes G.
Safir I.
Barbot F.
Laduranty J.
Tetrahedron Lett.
2004,
45:
1567
<A NAME="RZ20110SS-22">22</A>
Dai J.
Munakata M.
Wu L.-P.
Sowa TK.
Suenaga Y.
Inorg. Chim.
Acta
1997,
258:
65
<A NAME="RZ20110SS-23">23</A>
CCDC 778351 contains the supplementary
crystallographic data for compound 5a.
These data can be obtained free of charge at www.ccdc.cam.ac.uk/conts/retrieving.html
[or from
the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge
CB2 1EZ, UK; fax: +44(1223)336033,
E-mail: deposit@ccdc.cam.ac.uk].
<A NAME="RZ20110SS-24">24</A>
Hoffmann RW.
Chem.
Rev.
1989,
89:
1841