References
-
For reviews of domino and sequential
reactions, see:
-
1a
Tietze LF.
Beifuss U.
Angew. Chem.,
Int. Ed. Engl.
1993,
32:
131 ; Angew. Chem. 1993, 105, 137
-
1b
Tietze LF.
Chem. Rev.
1996,
96:
115
-
For reviews of work from our laboratory,
see:
-
2a
Langer P.
Chem.
Eur. J.
2001,
7:
3858
-
2b
Langer P.
Döring M.
Eur. J. Org. Chem.
2002,
221
-
2c
Langer P.
Synthesis
2002,
441
-
3a
Houben-Weyl .
Methods of
Organic Chemistry, Carbocyclic Three-Membered
Ring Compounds
Vol. E17:
de Meijere A.
Thieme;
Stuttgart:
1996.
-
3b
Kaiser EM.
Solter LE.
Schwarz RA.
Beard RD.
Hauser CR.
J. Am. Chem. Soc.
1971,
93:
4237
-
3c
Giblin GMP.
Ramcharitar SH.
Simpkins NS.
Tetrahedron Lett.
1988,
29:
4197
-
3d
Müller JFK.
Neuburger M.
Zehnder M.
Helv. Chim. Acta
1997,
80:
2182
-
4a
Langer P.
Freifeld I.
Org.
Lett.
2001,
3903
-
4b
Grangier G.
Aitken DJ.
Guillaume D.
Husson H.-P.
Tetrahedron Lett.
1994,
4355
-
4c
Benedetti F.
Berti F.
Risaliti A.
Tetrahedron
Lett.
1993,
6443
-
4d
Aitken DJ.
Royer J.
Husson H.-P.
J.
Org. Chem.
1990,
55:
2814
-
4e
Aitken DJ.
Royer J.
Husson H.-P.
Tetrahedron
Lett.
1988,
3315
-
4f
Mouzin G.
Cousse H.
Bonnaud B.
Synthesis
1978,
304
-
5a
Mussatto MC.
Savoia D.
Trombini C.
Umani-Ronchi A.
J.
Chem. Soc., Perkin Trans. 1
1980,
260
-
5b
Langer P.
Wuckelt J.
Döring M.
Görls H.
J. Org. Chem.
2000,
65:
3603
-
6a
Besson T.
Guillard J.
Rees CW.
Therisod M.
Chem. Commun.
1997,
881
-
6b
Leardini R.
Nanni D.
Pareschi P.
Tundo A.
Zanardi G.
J.
Org. Chem.
1997,
62:
8394
-
6c
Calestani G.
Capella L.
Leardini R.
Minozzi M.
Nanni D.
Papa R.
Romina R.
Zanardi G.
Tetrahedron
2001,
57:
7221
-
6d
Pfeiffer WD.
Pazdera P.
Hetzheim A.
Muecke J.
Pharmazie
1995,
50:
21
-
6e
Francis JE.
Cash WD.
Psychoyos S.
Ghai G.
Wenk P.
Friedmann RC.
Atkins C.
Warren V.
Furness P.
Hyun JL.
Stone GA.
Desai M.
Williams M.
J.
Med. Chem.
1988,
31:
1014
-
6f
Pavia MR.
Lobbestael SJ.
Taylor CP.
Hershenson FM.
Miskell DL.
J. Med. Chem.
1990,
33:
854
-
6g
Pfeiffer W.-D.
Hetzheim A.
Pazdera P.
Bodtke A.
Mücke J.
J.
Heterocycl. Chem.
1999,
36:
1327
-
6h
Blank J.
Kandt M.
Pfeiffer W.-D.
Hetzheim A.
Langer P.
Eur.
J. Org. Chem.
2003,
182
-
6i
Francis JE.
Cash WD.
Barbaz WD.
Bernard PS.
Lovell RA.
Mazzenga GC.
Friedmann RC.
Hyun JL.
Braunwalder AF.
Loo PS.
Bennett DA.
J.
Med. Chem.
1991,
34:
281
-
For related molecules, see:
-
7a
Peseke K.
Synthesis
1976,
386
-
7b
Bergman J.
Bergman S.
J. Org. Chem.
1985,
50:
1246
-
7c
Bajardi ML.
Daidone G.
Raffa D.
Plescia S.
Heterocycles
1986,
24:
1367
-
7d
Cheng Y.
Wang M.-X.
Gan W.-X.
Huang Z.-T.
Synth. Commun.
1996,
26:
475
-
7e
Neidlein R.
Sui Z.
Kramer W.
Boese R.
Rev. Roum. Chim.
1991,
36:
601
-
8a
Karwowsky JP.
Jackson M.
Rasmussen RR.
Humphrey PE.
Poddig JB.
Kohl WL.
Scherrr MH.
Kadam S.
McAlpine JB.
J.
Antibiot.
1993,
46:
374
-
8b
Hochlowki JE.
Mullally MM.
Spanton SG.
Whittern DN.
Hill P.
McAlpine JB.
J.
Antibiot.
1993,
46:
380
-
8c
Marsden SP.
Depew KM.
Danishefsky SJ.
J. Am. Chem. Soc.
1994,
116:
11143
-
9a
Penn J.
Mantle PG.
Bilton JN.
Sheppard RN.
J. Chem. Soc., Perkin Trans. 1
1992,
1495
-
9b
Takahashi C.
Matsushita T.
Doi M.
Minoura K.
Shingu T.
Kumeda Y.
Numata A.
J.
Chem. Soc., Perkin Trans. 1
1992,
1495
-
9c
Numata A.
Takahashi C.
Matsushita T.
Miyamoto T.
Kawai K.
Usami Y.
Matsumura E.
Inone M.
Ohishi H.
Shingu T.
Tetrahedron Lett.
1992,
33:
1621
-
9d
Wong S.
Musza LL.
Kydd GC.
Kullnig R.
Gillum AM.
Cooper R.
J. Antibiot.
1993,
46:
545
- 10
Bergman J.
Brynolf A.
Tetrahedron
1990,
46:
1295
-
11a
Clardy J.
Springer JP.
Büchi G.
Matsuo K.
Wightman R.
J. Am. Chem. Soc.
1975,
97:
663
-
11b
Büchi G.
Luk KC.
Kobbe B.
Townsend JM.
J.
Org. Chem.
1977,
42:
244
-
12a
Petersen S.
Herlinger H.
Tietze E.
Siefken W.
Angew.
Chem.
1962,
74:
855
-
12b
Johne S.
Jung B.
Pharmazie
1978,
33:
299
- 14 For comparison, see: Beckert R.
Gruner M.
Seidel I.
Kuban R.-J.
Monatsh.
Chem.
1989,
120:
1125
- 15
Dimroth O.
Liebigs
Ann. Chem.
1909,
364:
183
13
General procedure
A: To a THF suspension of 2-isothiocyanatobenzonitrile
(1a) and sodium hydride was added phenylacetonitrile
(2a) at 0 °C. The mixture was heated
at reflux for 72 h, cooled to room temperature and subsequently
an aqueous solution of NH4Cl (20 mL, 1 M) was added.
The organic and the aqueous layers were separated and the latter
was extracted three times with ether (30 mL). The combined organic
layers were dried (Na2SO4), filtered and the
solvent of the filtrate was removed in vacuo. The residue was recrystallized
from ethanol. Starting with 2a (0.351 g,
3.0 mmol), 1a (0.320 g, 2.0 mmol),
sodium hydride (0.096 g, 3.0 mmol) and 15 mL of THF, 3a was obtained
as a pale yellow solid (0.345 g, 62%, E/Z = 8:1).
General procedure B: To a THF solution
of phenylacetonitrile was added n-BuLi
(1.6 M solution in hexane) at 0 °C. After stirring for
1 h at 0 °C, the solution was cooled to -78 °C
and a THF solution of 2-isothiocyanatobenzonitrile
was added. After stirring for 30 min at -78 °C
an aqueous solution of NH4Cl (20 mL, 1 M) was added.
After warming to room temperature the organic and the aqueous layers
were separated and the latter was extracted three times with ether
(30 mL). The combined organic layers were dried (Na2SO4),
filtered and the solvent of the filtrate was removed in vacuo. The
residue was recrystallized from ethanol. Starting with 2a (0.28 g, 2.3 mmol), n-BuLi
(3.3 mL, 1.6 M), 1a (0.32 g, 2.0 mmol)
and 15 mL of THF, 3a was obtained as a
pale yellow solid (0.24 g, 43%).
1H
NMR (DMSO-d
6, 300 MHz): δ 7.24-7.41
(m, 3 H, CH), 7.43-7.65 (m, 5 H, CH), 8.68 (dd, 4
J = 1 Hz, 3
J = 8 Hz, 1 H, CH), 9.30 (s,
1 H, NH), 12.34 (s, 1 H, NH). 13C NMR (DMSO-d
6, 75 MHz, major isomer): δc 82.29
(C), 114.67 (CN), 116.30 (CH), 121.20 (C), 124.44, 124.95, 128.92, 129.21,
129.96 (CH), 132.64 (C), 133.69 (CH), 136.80, 141.75, 170.63 (C).
MS (70 eV): m/z (%):
277 (100, M+), 244(9), 217(18), 190(12), 165(4).
IR (KBr, cm-1): 3370 (s), 3207 (w),
3174 (m), 3143 (w), 3309 (m), 3068 (w), 2194 (s), 1608 (s), 1589
(s), 1551 (m), 1496 (s), 1449 (m), 1417 (m). Anal.: Calcd. for C16H11N3S:
C 69.29, H 4.00; found C 69.64, H 3.97.
