RSS-Feed abonnieren
Bitte kopieren Sie die angezeigte URL und fügen sie dann in Ihren RSS-Reader ein.
https://www.thieme-connect.de/rss/thieme/de/10.1055-s-00000083.xml
Synlett 2010(7): 1104-1106
DOI: 10.1055/s-0029-1219566
DOI: 10.1055/s-0029-1219566
LETTER
© Georg Thieme Verlag
Stuttgart ˙ New York
Synthesis of Symmetrical Ureas by (Diacetoxyiodo)benzene-Induced Hofmann Rearrangement
Weitere Informationen
Received
22 January 2010
Publikationsdatum:
02. März 2010 (online)
Publikationsverlauf
Publikationsdatum:
02. März 2010 (online)
Abstract
Amides undergo Hofmann rearrangement by treatment with (diacetoxyiodo)benzene (DAIB) to provide symmetrical ureas in a simple and robust transformation.
Key words
Hofmann rearrangement - ureas - carbamates - diacetoxyiodobenzene
-
1a
Vachal P.Jacobsen EN. J. Am. Chem. Soc. 2002, 124: 10012 -
1b
Yang D.Chen Y.-C.Zhu N.-Y. Org. Lett. 2004, 6: 1577 -
1c
Taylor MS.Jacobsen EN. J. Am. Chem. Soc. 2004, 126: 10558 -
1d
Yoon TP.Jacobsen EN. Angew. Chem. Int. Ed. 2005, 44: 466 -
1e
Fuerst DE.Jacobsen EN. J. Am. Chem. Soc. 2005, 127: 8964 -
1f
McCooey SH.Connon SJ. Angew. Chem. Int. Ed. 2005, 44: 6367 -
1g
Taylor MS.Tokunaga N.Jacobsen EN. Angew. Chem. Int. Ed. 2005, 44: 6700 -
1h
Xu X.Furukawa T.Okino T.Miyabe H.Takemoto Y. Chem. Eur. J. 2006, 12: 466 -
1i
Lalonde MP.Chen Y.Jacobsen EN. Angew. Chem. Int. Ed. 2006, 45: 6366 -
1j
Han C.Porco JA. Org. Lett. 2007, 9: 1517 -
1k
Tan KL.Jacobsen EN. Angew. Chem. Int. Ed. 2007, 46: 1315 -
1l
Procuranti B.Connon SJ. Chem. Commun. 2007, 1421 -
1m
Shi Y.-L.Shi M. Adv. Synth. Catal. 2007, 349: 2129 -
1n
Rampalakos C.Wulff WD. Adv. Synth. Catal. 2008, 350: 1785 -
1o
Yalalov DA.Tsogoeva SB.Shubina TE.Martynova IM.Clark T. Angew. Chem. Int. Ed. 2008, 47: 6624 -
1p
Fang Y.-Q.Jacobsen EN. J. Am. Chem. Soc. 2008, 130: 5660 -
1q
Andrés JM.Manzano R.Pedrosa R. Chem. Eur. J. 2008, 14: 5116 -
1r
Reisman SE.Doyle AG.Jacobsen EN. J. Am. Chem. Soc. 2008, 130: 7198 -
1s
Alemán J.Milelli A.Cabrera S.Reyes E.Jørgensen KA. Chem. Eur. J. 2008, 14: 10958 -
1t
Kotecki BJ.Fernando DP.Haight AR.Lukin KA. Org. Lett. 2009, 11: 947 -
1u
Wang F.Liu X.Cui X.Xiong Y.Zhou X.Feng X. Chem. Eur. J. 2009, 15: 589 -
1v
Reis Ö.Eymur S.Reis B.Demir AS. Chem. Commun. 2009, 1088 - For reviews, see:
-
2a
Taylor MS.Jacobsen EN. Angew. Chem. Int. Ed. 2006, 45: 1520 -
2b
Connon SJ. Chem. Commun. 2008, 2499 -
2c
Zhang Z.Schreiner PR. Chem. Soc. Rev. 2009, 38: 1187 -
3a
Batt DG.Houghton GC.Roderick J.Santella JB.Wacker DA.Welch PK.Orlovsky YI.Wadman EA.Trzaskos JM.Davies P.Decicco CP.Carter PH. Bioorg. Med. Chem. Lett. 2004, 15: 787 -
3b
Vidaluc J.-L, andBigg D. inventors; USPTO 5288758. -
3c
Rautenberg W,Harting J,Greiner H,Bartoszyk G,Böttcher H,Van Amsterdam C, andMatzen L. inventors; EP 1140898. -
3d
Kaplan AP, andGupta V. inventors; USPTO 20080306048. -
4a
Bankston D.Dumas J.Natero R.Riedl B.Monahan M.-K.Sibley R. Org. Process Res. Dev. 2002, 6: 777 -
4b
Clark JW.Eder JP.Ryan D.Lathia C.Lenz H.-J. Clin. Cancer Res. 2005, 11: 5472 -
4c
Wilhelm S.Carter C.Lynch M.Lowinger T.Dumas J.Smith RA.Schwartz B.Simantov R.Kelley S. Nat. Rev. Drug Discovery 2006, 5: 835 -
4d
Murphy DA.Makonnen S.Lassoued W.Feldman MD.Carter C.Lee WMF. Am. J. Pathol. 2006, 169: 1875 -
4e
Steinbild S.Mross K.Frost A.Morant R.Gillessen S.Dittrich C.Strumberg D.Hochhaus A.Hanauske A.-R.Edler L.Burkholder I.Scheulen M. Br. J. Cancer 2007, 97: 1480 -
5a
Fabian MA.Biggs WH.Treiber DK.Atteridge CE.Azimioara MD.Benedetti MG.Carter TA.Ciceri P.Edeen PT.Floyd M.Ford JM.Galvin M.Gerlach JL.Grotzfeld RM.Herrgard S.Insko DE.Insko MA.Lai AG.Lélias J.-M.Mehta SA.Milanov ZV.Velasco AM.Wodicka LM.Patel HK.Zarrinkar PP.Lockhart DJ. Nat. Biotechnol. 2005, 23: 329 -
5b
Quesada AR.Munoz-Chápuli R.Medina MA. Med. Res. Rev. 2006, 26: 483 -
5c
Liao JJ.-L. J. Med. Chem. 2007, 50: 409 -
6a
Jackson RC.Weber G. Nature 1975, 256: 331 -
6b
Markland W.McQuaid TJ.Jain J.Kwong AD. Antimicrob. Agents Chemother. 2000, 44: 859 -
6c
Gu HH.Iwanowicz EJ.Guo J.Watterson SH.Shen Z.Pitts WJ.Dhar TGM.Fleener CA.Rouleau K.Sherbina NZ.Witmer M.Tredup J.Hollenbaugh D. Bioorg. Med. Chem. Lett. 2002, 12: 1323 -
7a
Rudzevich Y.Cao Y.Rudzevich V.Böhmer V. Chem. Eur. J. 2008, 14: 3346 -
7b
Chauhan SMS.Bisht T.Garg B. Tetrahedron Lett. 2008, 49: 6646 -
7c
dos Santos CMG.McCabe T.Watson GW.Kruger PE.Gunnlaugsson T. J. Org. Chem. 2008, 73: 9235 -
7d
Ye S.Ding Q.Wang Z.Zhou H.Wu J. Org. Biomol. Chem. 2008, 6: 4406 -
7e
Cui Y.-M.Yasutomi E.Otani Y.Yoshinaga T.Ido K.Sawada K.Ohwada T. Bioorg. Med. Chem. Lett. 2008, 18: 5201 -
7f
Clayden J.Lemiègre L.Morris GA.Pickworth M.Snape PJ.Jones LH. J. Am. Chem. Soc. 2008, 130: 15193 - Reviews:
-
8a
Stang PJ.Zhdankin VV. Chem. Rev. 2008, 108: 5299 -
8b
Zhdankin VV. ARKIVOC 2009, (i): 1 -
9a
Loudon GM.Radhakrishna AS.Almond MR.Blodgett JK.Boutin RH. J. Org. Chem. 1984, 49: 4272 -
9b
Lazbin IM.Koser GF. J. Org. Chem. 1986, 51: 2669 -
9c
Vasudevan A.Koser GF. J. Org. Chem. 1988, 53: 5158 - 11 See also:
Moriarty RM.Chany CJ.Vaid RK.Prakash O.Tuladhar SM. J. Org. Chem. 1993, 58: 2478 - 12
Irschik H.Gerth K.Höfle G.Kohl W.Reichenbach H. J. Antibiot. 1983, 36: 1651 - 13
Irschik H.Jansen R.Höfle G.Gerth K.Reichenbach H. J. Antibiot. 1985, 38: 145
References and Notes
Representative Procedure (Table 1, Entry 1): A solution of benzamide (121 mg, 1.00 mmol), PhI(OAc)2 (DAIB; 419 mg, 1.30 mmol) and H2O (54 µL, 3.00 mmol) in CH2Cl2 (10 mL) was stirred at ambient temperature for 16 h. The resulting solution was stirred at 40 ˚C for 1 h, then the solution was concentrated under vacuum and the remaining residue was purified by column chromatography on silica gel (hexane-EtOAc, 3:1) to yield the corresponding urea as a colorless solid (52.4 mg, 49%).