Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000083.xml
Synlett 2011(16): 2307-2310
DOI: 10.1055/s-0030-1261219
DOI: 10.1055/s-0030-1261219
LETTER
© Georg Thieme Verlag
Stuttgart ˙ New York
Facile Synthesis of Highly Substituted Iminocyclopentenes: A Novel Isocyanide-Based Three-Component Condensation Reaction
Further Information
Received
16 May 2011
Publication Date:
08 September 2011 (online)
Publication History
Publication Date:
08 September 2011 (online)
![](https://www.thieme-connect.de/media/synlett/201116/lookinside/thumbnails/10.1055-s-0030-1261219-1.jpg)
Abstract
The reaction of alkoxymethylenemalononitrile with dialkyl acetylenedicarboxylates (DAAD) and cyclohexylisocyanide results in a three-component condensation reaction in which the alkoxymethylenemalononitrile group acts as a dipolarophile, producing highly functionalized iminocyclopentenes under mild conditions in high yields.
Key words
alkoxymethylenemalononitrile - dialkyl acetylenedicarboxylates - isocyanides - iminocyclopentenes
- 1
Gao F.Zhang G.Zhang S.Cheng Y.Shi Z.Li Y.Gao J. Tetrahedron 2007, 63: 3973 -
2a
Ngouansavanh T.Zhu JP. Angew. Chem. Int. Ed. 2007, 46: 5775 -
2b
Yan CG.Song XK.Wang QF.Sun J.Siemeling U.Bruhn C. Chem. Commun. 2008, 1440 - 3
Multicomponent Reactions
Zhu J.Bienayme H. Wiley-WCH; Weinheim: 2005. - 4
Li-Rong W.Chem J.Ming L.Huai-Yuan X. Tetrahedron 2009, 65: 1287 - 5
Dömling A.Ugi I. Angew. Chem. Int. Ed. 2000, 39: 3198 - 6
Sutharchanadevi M.Murugan R. In Comprehensive Heterocyclic Chemistry II Vol. 3:Katritzky AR.Rees CW.Scriven EFV. Pergamon; London: 1996. p.221-260 ; and references cited therein -
7a
Semple JE.Rowley DC.Brunck TK.Ripka WC. Bioorg. Med. Chem. Lett. 1997, 7: 315 -
7b
Harmat NJS.Di Bugno C.Criscuoli M.Giorgi R.Lippi A.Martinelli A.Monti S.Subissi A. Bioorg. Med. Chem. Lett. 1998, 8: 1249 - 8
Thorstensson F.Wångsell F.Kvarnsträm I.Vrang L.Hamelink E.Jansson K.Hallberg A.Rosenquist A.Samuelsson B. Bioorg. Med. Chem. 2007, 15: 827 - 9
Giomi D.Cordero FM.Machetti F. In Comprehensive Heterocyclic Chemistry III Vol. 4:Katritzky AR.Ramsden CA.Scriven EFV.Taylor RJK. Elsevier Science; Oxford: 2008. p.365-483 ; and references cited therein - 10
Kalita PK.Baruah B.Bhuyan PJ. Tetrahedron Lett. 2006, 47: 7779 -
11a
Jaeger V.Buss V.Schwab W. Tetrahedron Lett. 1978, 19: 3133 -
11b
Kotera K.Takano Y.Mutsuura A.Kitahonoki K. Tetrahedron 1970, 26: 539 -
11c
Lang SA.Lin YI. In Comprehensive Heterocyclic Chemistry Vol. 6:Katritzky AR.Rees CW. Pergamon Press; Oxford: 1984. -
12a
Kominami G.Nakamura M.Chomei N.Takada S.
J. Pharm. Biomed. Anal. 1999, 20: 145 -
12b
Kawasaki K.Eigyo M.Ikeda M.Kihara T.Koike K.Matsushita A.Murata S.Shiomi T.Takada S.Yasui M. Prog. Neuro-Physicopharmacol. Biol. Psychiat. 1996, 20: 1413 - 13
Marcus E.Chan JK.Hughes JL. J. Chem. Eng. Data 1967, 12: 151 - 14
Chantegrel B.Nadi AI.Gelin S. J. Heterocycl. Chem. 1985, 22: 1127 - 15
Schneider R.Gérardin P.Loubinoux B. J. Heterocycl. Chem. 1994, 31: 797 - 16
Adib M.Sheikhi E.Haghshenas P.Bijanzadeh HR. Synlett 2010, 2775 - 17
Shaabani A.Rezayan AH.Rahmati A.Sarvary A. Synlett 2007, 1458 - 18
Nair V.Rajeev S.Menon PB.Beneesh V.Sreekumar Bindu S. Org. Lett. 2004, 6: 767 -
19a
Esmaeili AA.Bodaghi A. Tetrahedron 2003, 59: 1169 -
19b
Esmaeili AA.Darbanian M. Tetrahedron 2003, 59: 5545 -
19c
Esmaeili AA.Zendegani H. Tetrahedron 2005, 61: 4031 -
20a
Esmaeili AA.Amini S.Bodaghi A. Synlett 2007, 1452 -
20b
Esmaeili AA.Nasseri MA.Vesalipoor H.Bijanzadeh H. ARKIVOC 2008, (xv): 343 -
20c
Esmaili AA.Vesalipoor H. Synthesis 2009, 1635 - 21
Esmaeili AA.Hosseinabadi R.Habibi A. Synlett 2010, 1477 - 22
Silverstein RM.Webster FX.Kiemle DJ. Spectrometric Identification of Organic Compounds 7 ed.: John Wiley and Sons; New York: 2005. p.103