Abstract
Efficient and divergent one-pot synthesis of cyclopropyl amides
and esters from readily available 1-acetylcyclopropanes via iodoform
reaction based on the selection of reaction conditions is reported.
A series of substituted cyclopropyl amides were synthesized from
1-acetylcyclopropanes, iodine, and ammonia in water in the presence
of K2 CO3 in good yields, whereas substituted
cyclopropyl esters were obtained from the reaction of 1-acetylcyclopropanes with
iodine and alcohols in the presence of DBU.
Key words
cyclopropanes - iodoform reaction - iodine - amide - water
References
For reviews on cyclopropanes, see:
1a
Wong HNC.
Hon MY.
Tse CW.
Yip YC.
Tanko J.
Hudlicky T.
Chem.
Rev.
1989,
89:
165
1b
Kulinkovich OG.
Chem. Rev.
2003,
103:
2597
1c
Brackmann F.
de Meijere A.
Chem. Rev.
2007,
107:
4493
1d
Gnad F.
Reiser O.
Chem. Rev.
2003,
103:
1603
1e
Noyori R.
Angew.
Chem. Int. Ed.
2002,
41:
2008
2a
Vinogradov MG.
Kaigorodova LN.
Chel’tsova-Bebutova GV.
Gorshkova LS.
Starostin EK.
Nikishin GL.
Ignatenko AV.
Shapiro EA.
Russ. Chem. Bull.
1995,
44:
167
2b
Kaneko H.
J.
Agric. Food Chem.
2011,
59:
2786
2c
Graham DW.
Ashton WT.
Barash L.
Brown JE.
Brown RD.
Canning LF.
Chen A.
Springer JP.
Rogers EF.
J. Med. Chem.
1987,
30:
1074
2d
Krief A.
Froidbisea A.
Tetrahedron
2004,
60:
7637
For reviews, see:
3a
Hoveyda AH.
Evans DA.
Fu GC.
Chem. Rev.
1993,
93:
1307
3b
Charette AB.
Marcoux J.-F.
Synlett
1995,
1197
3c
Lautens M.
Klute W.
Tam W.
Chem.
Rev.
1996,
96:
49
3d
Charette AB.
Lebel H. In Comprehensive Asymmetric Catalysis
Jacobsen EN.
Pfaltz A.
Yamamoto H.
Springer-Verlag;
Berlin:
1999.
Chap.
16.3.
3e
Lebel H.
Marcoux J.-F.
Molinaro C.
Charette AB.
Chem. Rev.
2003,
103:
977
For references, see:
4a
Simmons HE.
Smith RD.
J.
Am. Chem. Soc.
1958,
80:
5323
4b
Simmons HE.
Smith RD.
J.
Am. Chem. Soc.
1959,
81:
4256
4c
Rawson RJ.
Harrison IT.
J.
Org. Chem.
1970,
35:
2057
4d
Nishimura J.
Furukawa J.
Kawabata N.
Kitayama M.
Tetrahedron
1971,
27:
1799
4e
Friedrich EC.
Lunetta SE.
Lewis EJ.
J. Org. Chem.
1989,
54:
2388
4f
Charette AB.
Marcoux J.-F.
Molinaro C.
Beauchemin A.
Brochu C.
Isabel E.
J. Am. Chem.
Soc.
2000,
122:
4508
5a
Shimamoto K.
Ishida M.
Shinozaki H.
Ohfune Y.
J.
Org. Chem.
1991,
56:
4167
5b
Shimamoto K.
Ohfune Y.
Tetrahedron Lett.
1989,
30:
3802
5c
Hanessian S.
Murray PJ.
J. Org. Chem.
1987,
52:
1170
5d
Vangveravong S.
Nichols DE.
J. Org. Chem.
1995,
60:
3409
5e
Pietruszka J.
Widenmeyer M.
Synlett
1997,
977
5f
Luithle JEA.
Pietruszka J.
J.
Org. Chem.
1999,
64:
8287
5g
Pietruszka J.
Witt A.
J. Chem. Soc., Perkin Trans. 1
2000,
4293
5h
Luithle JEA.
Pietruszka J.
J.
Org. Chem.
2000,
65:
9194
6a
de Meijere A.
Bagutski V.
Zeuner F.
Fischer UK.
Rheinberger V.
Moszner N.
Eur.
J. Org. Chem.
2004,
3669
6b
Yang Y.
Shi M.
J. Org. Chem.
2005,
70:
8645
6c
Su J.
Xiong J.
Liang S.
Qiu G.
Feng X.
Teng H.
Wu L.
Hu X.
Synth.
Commun.
2006,
36:
693
6d
Ronsisvalle G.
Marrazzo A.
Prezzavento O.
Pasquinucci L.
Falcucci B.
Toro RD.
Spampinato S.
Bioorg.
Med. Chem.
2000,
8:
1503
7a
Pan W.
Dong D.
Wang K.
Zhang J.
Wu R.
Xiang D.
Liu Q.
Org.
Lett.
2007,
9:
2421
7b
Fu X.
Huang P.
Zhou G.
Hu Y.
Dong D.
Tetrahedron
2011,
67:
6347
7c
Wang K.
Fu X.
Liu J.
Liang Y.
Dong D.
Org. Lett.
2009,
11:
1015
7d
Wang K.
Xiang D.
Liu J.
Pan W.
Dong D.
Org. Lett.
2008,
10:
1691
For Iodoform reactions, see:
8a
Fuson RC.
Bull BA.
Chem.
Rev.
1934,
15:
275
8b
Fuson RC.
Tullock CW.
J.
Am. Chem. Soc.
1934,
56:
1638
8c
Arnold RT.
Buckles R.
Stoltenberg J.
J. Am. Chem. Soc.
1944,
66:
208
For the conversion of acetyl into amide and ester group, see:
8d
Cao L.
Ding J.
Gao M.
Wang Z.
Li J.
Wu A.
Org.
Lett.
2009,
11:
3810
8e
Yin G.
Gao M.
Wang Z.
Wu Y.
Wu A.
Bull. Chem. Soc.
Jpn.
2008,
81:
369
9 For the preparation of 1-acetyl-1-carbamoylcyclopropanes, see: Zhang Z.
Zhang Q.
Sun S.
Xiong T.
Liu Q.
Angew.
Chem. Int. Ed.
2007,
46:
1726
10a
Aqueous-Phase Organometallic Catalysis: Concepts
and Applications
Cornils B.
Herrmann WA.
Wiley-VCH;
Weinheim:
1998.
10b
Organic
Synthesis in Water
Grieco PA.
Blackie
Academic and Professional;
London:
1998.
10c
Organic
Reactions in Aqueous Media
Li C.-J.
Chan T.-H.
Wiley;
New
York:
1997.
10d
Kobayashi S.
Manabe K. In Stimulating
Concepts in Chemistry
Shibasaki M.
Stoddart JF.
Vögtle F.
Wiley-VCH;
Weinheim:
2000.
11a
Li CJ.
Chem. Rev.
1993,
93:
2023
11b
Fringuelli F.
Piermatti O.
Pizzo F.
Vaccaro L.
Eur. J. Org. Chem.
2001,
439
11c
Kobayashi S.
Manabe K.
Acc. Chem. Res.
2002,
35:
209
12a
Manabe K.
Mori Y.
Kobayashi S.
Synlett
1999,
1401
12b
Manabe K.
Kobayashi S.
Org. Lett.
1999,
1:
1965
12c
Otto S.
Engberts JBSN.
Kwak JCT.
J. Am. Chem. Soc.
1998,
120:
9517
12d
Rispens T.
Engberts JBSN.
Org.
Lett.
2001,
3:
941
12e
Manabe K.
Sun XM.
Kobayashi S.
J.
Am. Chem. Soc.
2001,
123:
10101
12f
Ouyang Y.
Dong D.
Yu H.
Liang Y.
Liu Q.
Adv. Synth.
Catal.
2006,
348:
206
13 The relative configurations of cis
-1k ,
trans
-1l , cis
-2k , and trans
-2l were determined by NOESY, see Supporting Information.
For selected work on the conversion
of amide into cyano group, see:
14a
Mowry DT.
Chem. Rev.
1948,
42:
189
14b
Rickborn B.
Jensen FR.
J. Org. Chem.
1962,
27:
4608
14c
Lehnert W.
Tetrahedron
Lett.
1971,
19:
1501
14d
Ellzey SE.
Mack CH.
Connick WJ.
J. Org. Chem.
1967,
32:
846
For selected examples on ring-opening
or ring-enlargement reactions of cyclopropanes, see:
15a
Bernard AM.
Frongia A.
Piras PP.
Secci F.
Spiga M.
Org. Lett.
2005,
7:
4565
15b
Ogoshi S.
Nagata M.
Kurosawa H.
J.
Am. Chem. Soc.
2006,
128:
5350
15c
Liu L.
Montgomery J.
J. Am. Chem. Soc.
2006,
128:
5348
15d
Ma S.
Zhang J.
Angew. Chem. Int. Ed.
2003,
42:
183
For selected references on Vilsmeier
reagents, see:
16a
Marson CM.
Tetrahedron
1992,
48:
3659
16b
Meth-Cohn O.
Tarnowski B.
Adv. Heterocycl. Chem.
1982,
31:
207
16c
Reichardt C.
J.
Prakt. Chem.
1999,
341:
609
16d
Gangadasu B.
Narender P.
Kumar SB.
Ravinder M.
Rao BA.
Ramesh C.
Raju BC.
Rao VJ.
Tetrahedron
2006,
62:
8398
16e
Thomas AD.
Asokan CV.
Tetrahedron
2004,
60:
5069
17a
Johnson CR.
Lockard JP.
Kennedy ER.
J.
Org. Chem.
1980,
45:
264
17b
Zhang Z.
Xue C.
Liu X.
Zhang Q.
Liu Q.
Tetrahedron
2011,
67:
7081