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Synlett 2011(15): 2200-2202
DOI: 10.1055/s-0030-1261179
DOI: 10.1055/s-0030-1261179
LETTER
© Georg Thieme Verlag
Stuttgart ˙ New York
Solvent-Free Synthesis of Enamines from Alkyl Esters of Propiolic or But-2-yne Dicarboxylic Acid in a Ball Mill
Weitere Informationen
Received
8 June 2011
Publikationsdatum:
12. August 2011 (online)
Publikationsverlauf
Publikationsdatum:
12. August 2011 (online)

Abstract
A solvent-free method for the addition of amines to dialkylacetylendicarboxylates or alkylpropiolates using a planetary ball mill was developed. Conversion of educts was quantitative within five minutes without use of any catalyst or base. Beside the E-/Z-isomers, no side products were formed.
Key words
addition - amines - alkynes - enamines - green chemistry
- Supporting Information for this article is available online:
- Supporting Information
-
1a
Mohri K.Kanie A.Horiguchi Y.Isobe K. Heterocycles 1999, 51: 2377 -
1b
Borisov AA.Rozinov VG.Bozhenkov GV.Larina LI. Russ. J. Gen. Chem. 2004, 74: 1822 -
1c
Al-Saleh B.Makhseed S.Hassaneen HME.Hilmy Elnagdi M. Synthesis 2006, 59 -
1d
Chepyshev SV.Mazurkevich YN.Lebed OS.Prosyanik AV. Chem. Heterocycl. Compd. 2007, 43: 844 -
1e
Zang M.Jiang H.-F. Eur. J. Org Chem. 2008, 3519 -
1f
Shi Z.Zhang C.Li S.Pan D.Ding S.Cui Y.Jiao N. Angew. Chem. Int. Ed. 2009, 48: 4572 -
1g
Matsumoto S.Mori T.Akazome M. Synthesis 2010, 3615 -
1h
Sirijindalert T.Hansuthirakul K.Rashatasakhon P.Sukwattanasinitt M.Ajavakom A. Tetrahedron 2010, 66: 5161 -
1i
Sun J.Xia E.-Y.Wu Q.Yan C.-G. Org. Lett. 2010, 12: 3678 -
2a
Kazi SA.Kelso GF.Harris S.Boysen RI.Chowdhury J.Hearn M. Tetrahedron 2010, 66: 9461 -
2b
Mazzoni O.Esposito G.Diurno MV.Brancaccio D.Carotenuto A.Grieco P.Novellino E.Filippelli W. Arch. Pharm. 2010, 343: 561 -
3a
Huisgen R.Herbig K.Siegl A.Huber H. Chem. Ber. 1966, 99: 2526 -
3b
Cossu S.De Lucchi O.Durr R. Synth. Commun. 1996, 26: 4597 -
3c
Ziyaei-Halimehjani A.Saidi MR. Tetrahedron Lett. 2008, 49: 1244 - 4
Zhu Q.Jiang H.Li J.Zhang M.Wang X.Qi C. Tetrahedron 2009, 65: 4604 -
5a
Um I.-H.Yuk S.-M.Yoon S.-I. Bull. Korean Chem. Soc. 2000, 21: 553 -
5b
Nori-Shargh D.Soltani B.Saroogh-Farahani N.Deyhimi F. Int. J. Chem. Kin. 2006, 38: 144 - For recent reviews, see:
-
6a
Rodriguez B.Bruckmann A.Rantanen T.Bolm C. Adv. Synth. Catal. 2007, 349: 2213 -
6b
Bruckmann A.Krebs A.Bolm C. Green Chem. 2008, 10: 1131 -
6c
Kaupp G. J. Phys. Org. Chem. 2008, 21: 630 -
6d
Tanaka K. Solvent-Free Organic Synthesis 2nd ed.: Wiley-VCH; Weinheim: 2009. -
6e
Stolle A.Szuppa T.Leonhardt SES.Ondruschka B. Chem. Soc. Rev. 2011, 40: 2317 -
7a
Feldbæk Nielsen S.Peters D.Axelsson O. Synth. Commun. 2000, 30: 3501 -
7b
Rodriguez B.Bruckmann A.Bolm C. Chem. Eur. J. 2007, 13: 4710 -
7c
Declerck V.Nun P.Martinez J.Lamaty F. Angew. Chem. Int. Ed. 2009, 48: 9318 -
7d
Bruckmann A.Rodriguez B.Bolm C. CrystEngComm 2009, 11: 404 -
7e
Schneider F.Ondruschka B. ChemSusChem 2008, 1: 622 -
7f
Wang G.-W.Gao J. Org. Lett. 2009, 11: 2385 -
7g
Schneider F.Stolle A.Ondruschka B.Hopf H. Org. Process Res. Dev. 2009, 13: 44 -
7h
Fulmer DA.Shearouse WC.Medonza ST.Mack J. Green Chem. 2009, 11: 1821 -
7i
Schneider F.Szuppa T.Stolle A.Ondruschka B.Hopf H. Green Chem. 2009, 11: 1894 -
7j
Waddell DC.Thiel I.Clark TD.Marcum ST.Mack J. Green Chem. 2010, 12: 209 -
7k
Szuppa T.Stolle A.Ondruschka B.Hopfe W. Green Chem. 2010, 12: 1288 -
7l
Thorwirth R.Stolle A.Ondruschka B. Green Chem. 2010, 12: 985 -
7m
Szuppa T.Stolle A.Ondruschka B.Hopfe W. ChemSusChem 2010, 3: 1181 -
7n
Thorwirth R.Stolle A.Ondruschka B.Wild A.Schubert US. Chem. Commun. 2011, 47: 4370 -
7o
Schmidt R.Thorwirth R.Szuppa T.Stolle A.Ondruschka B.Hopf H. Chem. Eur. J. 2011, 17: 8129