-
1
-
-
84860875380
-
-
Gewald, K.; Schinke, E.; Böttcher, H. Chem. Ber. 1966, 99, 94.
-
(1966)
Chem. Ber
, vol.99
, pp. 94
-
-
Gewald, K.1
Schinke, E.2
Böttcher, H.3
-
2
-
-
0032921759
-
-
For a review on the synthesis of 2-aminothiophenes by Gewald reaction, see: (a) Sabnis, R. W.; Rangnekar, D. W.; Sonawane, N. D. J. Heterocycl. Chem. 1999, 36, 333.
-
For a review on the synthesis of 2-aminothiophenes by Gewald reaction, see: (a) Sabnis, R. W.; Rangnekar, D. W.; Sonawane, N. D. J. Heterocycl. Chem. 1999, 36, 333.
-
-
-
-
3
-
-
38349158743
-
-
For a review on multicomponent reactions of carbonyl compounds and derivatives of cyanoacetic acid, see: b
-
For a review on multicomponent reactions of carbonyl compounds and derivatives of cyanoacetic acid, see: (b) Shestopalov, A. M.; Shestopalov, A. A.; Rodinovskaya, L. A. Synthesis 2008, 1.
-
(2008)
Synthesis
, pp. 1
-
-
Shestopalov, A.M.1
Shestopalov, A.A.2
Rodinovskaya, L.A.3
-
5
-
-
27744528229
-
-
(a) LaPorte, M. G.; Lessen, T. A.; Leister, L.; Cebzanov, D.; Amparo, E.; Faust, C.; Ortlip, D.; Bailey, T. R.; Nitz, T. J.; Chunduru, S. K.; Young, D. C.; Burns, C. J. Bioorg. Med. Chem. Lett. 2006, 16, 100.
-
(2006)
Bioorg. Med. Chem. Lett
, vol.16
, pp. 100
-
-
LaPorte, M.G.1
Lessen, T.A.2
Leister, L.3
Cebzanov, D.4
Amparo, E.5
Faust, C.6
Ortlip, D.7
Bailey, T.R.8
Nitz, T.J.9
Chunduru, S.K.10
Young, D.C.11
Burns, C.J.12
-
6
-
-
0038400425
-
-
(b) Gütschow, M.; Kuerschner, L.; Neumann, U.; Pietsch, M.; Löser, R.; Koglin, N.; Eger, K. J. Med. Chem. 1999, 42, 5437.
-
(1999)
J. Med. Chem
, vol.42
, pp. 5437
-
-
Gütschow, M.1
Kuerschner, L.2
Neumann, U.3
Pietsch, M.4
Löser, R.5
Koglin, N.6
Eger, K.7
-
7
-
-
0000176689
-
-
Koike, K.; Jia, Z.; Nikaido, T.; Liu, Y.; Zhao, Y.; Guo, D. Org. Lett. 1999, 1, 197.
-
(1999)
Org. Lett
, vol.1
, pp. 197
-
-
Koike, K.1
Jia, Z.2
Nikaido, T.3
Liu, Y.4
Zhao, Y.5
Guo, D.6
-
8
-
-
2442530818
-
-
(a) Bonauer, C.; Zabel, M.; König, B. Org. Lett. 2004, 6, 1349.
-
(2004)
Org. Lett
, vol.6
, pp. 1349
-
-
Bonauer, C.1
Zabel, M.2
König, B.3
-
9
-
-
0030852173
-
-
(b) Gervay, J.; Ramamoorthy, P. S.; Mamuya, N. N. Tetrahedron 1997, 53, 11039.
-
(1997)
Tetrahedron
, vol.53
, pp. 11039
-
-
Gervay, J.1
Ramamoorthy, P.S.2
Mamuya, N.N.3
-
10
-
-
0031550819
-
-
(c) Gervay, J.; Flaherty, T. M.; Nguyen, C. Tetrahedron Lett. 1997, 38, 1493.
-
(1997)
Tetrahedron Lett
, vol.38
, pp. 1493
-
-
Gervay, J.1
Flaherty, T.M.2
Nguyen, C.3
-
11
-
-
4644244412
-
-
(d) Baldauf, C.; Günther, R.; Hofmann, H.-J. J. Org. Chem. 2004, 69, 6214.
-
(2004)
J. Org. Chem
, vol.69
, pp. 6214
-
-
Baldauf, C.1
Günther, R.2
Hofmann, H.-J.3
-
12
-
-
33751036480
-
-
(e) Sünnemann, H. W.; Hofmeister, A.; Magull, J.; de Meijere, A. Chem. Eur. J. 2006, 12, 8336.
-
(2006)
Chem. Eur. J
, vol.12
, pp. 8336
-
-
Sünnemann, H.W.1
Hofmeister, A.2
Magull, J.3
de Meijere, A.4
-
14
-
-
0001796781
-
-
For reviews of donor-acceptor-substituted cyclopropanes, see: b
-
For reviews of donor-acceptor-substituted cyclopropanes, see: (b) Reissig, H.-U. Top. Curr. Chem. 1988, 144, 73.
-
(1988)
Top. Curr. Chem
, vol.144
, pp. 73
-
-
Reissig, H.-U.1
-
18
-
-
0001475658
-
-
(c) Grimm, E. L.; Zschiesche, R.; Reissig, H.-U. J. Org. Chem. 1985, 50, 5543.
-
(1985)
J. Org. Chem
, vol.50
, pp. 5543
-
-
Grimm, E.L.1
Zschiesche, R.2
Reissig, H.-U.3
-
20
-
-
0034841164
-
-
(e) Zimmer, R.; Ziemer, A.; Gruner, M.; Brüdgam, I.; Hartl, H.; Reissig, H.-U. Synthesis 2001, 1649.
-
(2001)
Synthesis
, pp. 1649
-
-
Zimmer, R.1
Ziemer, A.2
Gruner, M.3
Brüdgam, I.4
Hartl, H.5
Reissig, H.-U.6
-
22
-
-
33748324475
-
-
(g) Veljkovic, I.; Zimmer, R.; Reissig, H.-U.; Brüdgam, I.; Hartl, H. Synthesis 2006, 2677.
-
(2006)
Synthesis
, pp. 2677
-
-
Veljkovic, I.1
Zimmer, R.2
Reissig, H.-U.3
Brüdgam, I.4
Hartl, H.5
-
23
-
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58149331578
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Typical Procedure for the Synthesis of 2-Aminothiophene 4a Using the One-Pot/One-Stage Procedure Siloxycyclopropanecarboxylate 1a (0.209 g, 1.06 mmol, tert-butyl cyanoacetate (0.143 g, 1.01 mmol) and sulfur (0.032 g, 1.01 mmol) were suspended in MeOH (2 mL, then Et2NH (0.11 mL, 1.01 mmol) was added. The mixture was refluxed for 7 h, and then stirred overnight at r.t. After addition of water and EtOAc the layers were separated and the aqueous layer was extracted two times with EtOAc. The combined organic layers were dried with Na2SO4, filtered, and concentrated. Column chromatography (SiO2, hexane-EtOAc, 8:1 to 7:1 to 6:1) provided 0.180 g (66, 4a as a brownish oil. Analytical Data for tert-Butyl 2-Amino-5-(2-methoxy-2-oxoethyl)thiophene-3- carboxylate(4a) 1H NMR (500 MHz, CDCl3, δ, 1.50 [s, 9 H, C(CH3)3, 3.56 s, 2 H, CH2, 3
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4S (271.3): C, 53.12; H, 6.32; N, 5.16; S, 11.82. Found: C, 53.37; H, 6.43; N, 5.16; S, 11.95.
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24
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58149358665
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We also prepared thiophene 4a in 61% yield starting from commercially available aldehyde 2a using a one-pot/one-stage Gewald procedure (method A). Although the result is comparable with the yield we achieved with cyclopropane 1a the very high cost of aldehyde 2a (100 mg, 77 €) is almost prohibitive for large-scale preparations of 4a.
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We also prepared thiophene 4a in 61% yield starting from commercially available aldehyde 2a using a one-pot/one-stage Gewald procedure (method A). Although the result is comparable with the yield we achieved with cyclopropane 1a the very high cost of aldehyde 2a (100 mg, 77 €) is almost prohibitive for large-scale preparations of 4a.
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26
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1342302805
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For a review on recent development of peptide coupling reagents in organic synthesis, see
-
(a) For a review on recent development of peptide coupling reagents in organic synthesis, see: Han, S.-Y.; Kim, Y.-A. Tetrahedron 2004, 60, 2447.
-
(2004)
Tetrahedron
, vol.60
, pp. 2447
-
-
Han, S.-Y.1
Kim, Y.-A.2
-
27
-
-
0007193238
-
-
For a review on chemical synthesis of natural product peptides, see
-
(b) For a review on chemical synthesis of natural product peptides, see: Humphrey, J. M.; Chamberlin, A. R. Chem. Rev. 1997, 97, 2243.
-
(1997)
Chem. Rev
, vol.97
, pp. 2243
-
-
Humphrey, J.M.1
Chamberlin, A.R.2
-
29
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58149362039
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Alternatively, 7c was synthesized in 59% overall yield by a reversed reaction sequence.
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Alternatively, 7c was synthesized in 59% overall yield by a reversed reaction sequence.
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-
-
33
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0029930442
-
-
Burke, T. R.; Ye, B. Jr.; Akamatsu, M.; Ford, H.; Yan, X. Jr.; Kole, H. K.; Wolf, G.; Shoelson, S. E.; Roller, P. P. J. Med. Chem. 1996, 39, 1021.
-
(1996)
J. Med. Chem
, vol.39
, pp. 1021
-
-
Burke, T.R.1
Ye Jr., B.2
Akamatsu, M.3
Ford, H.4
Yan Jr., X.5
Kole, H.K.6
Wolf, G.7
Shoelson, S.E.8
Roller, P.P.9
-
34
-
-
0026709956
-
-
Mehta, A.; Jaouhari, R.; Benson, T. J.; Douglas, K. T. Tetrahedron Lett. 1992, 33, 5441.
-
(1992)
Tetrahedron Lett
, vol.33
, pp. 5441
-
-
Mehta, A.1
Jaouhari, R.2
Benson, T.J.3
Douglas, K.T.4
-
36
-
-
0001537514
-
-
Angew. Chem. 1991, 103, 1305.
-
(1991)
Angew. Chem
, vol.103
, pp. 1305
-
-
-
38
-
-
0000734566
-
-
Angew. Chem. 1993, 105, 1303.
-
(1993)
Angew. Chem
, vol.105
, pp. 1303
-
-
-
39
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58149342460
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During peptide couplings presented here we did not observe racemization of the amino acid moiety since subsequent couplings with a second amino acid provided only one diastereomer
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During peptide couplings presented here we did not observe racemization of the amino acid moiety since subsequent couplings with a second amino acid provided only one diastereomer.
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