A formal [4 + 4] complementary ambiphile pairing reaction: a new cyclization pathway for ortho-quinone methides.
A formal, one-pot [4 + 4] cyclization pathway for the generation of eight-membered sultams via in situ generation of an ortho-quinone methide (o-QM) is reported. The pairing of ambiphilic synthons in a complementary fashion is examined whereby o-fluorobenzenesulfonamides are merged with in situ generated o-QM in a formal [4 + 4] cyclization pathway to afford 5,2,1-dibenzooxathiazocine-2,2-dioxide scaffolds under microwave (mW) conditions. The method reported represents the first use of an o-QM in a formal hetero [4 + 4] cyclization.
Samarakoon
Thiwanka B
TB
Department of Chemistry, University of Kansas, 1251 Wescoe Hall Drive, Lawrence, Kansas 66045-7582, USA.
Hur
Moon Y
MY
Kurtz
Ryan D
RD
Hanson
Paul R
PR
D018360:Crystallography, X-Ray; D003500:Cyclization; D045563:Indolequinones / Q000138:chemical synthesis* / Q000737:chemistry; D008958:Models, Molecular; D015394:Molecular Structure; D013237:Stereoisomerism
D045563:Indolequinones; C068040:quinone methide
Angew Chem Int Ed Engl. 2008;47(22):4188-91
18435515
Chemistry. 2009;15(6):1300-8
19132705
Curr Med Chem. 2003 Jun;10(11):925-53
12678681
J Org Chem. 2004 Dec 24;69(26):9196-203
15609955
Org Lett. 2010 Mar 19;12(6):1216-9
20178346
J Am Chem Soc. 2008 Jul 23;130(29):9230-1
18582058
Org Lett. 2009 Feb 5;11(3):531-4
19115841
Org Lett. 2008 Jun 5;10(11):2223-6
18447383
Tetrahedron. 2009 Apr 18;65(16):3180-3188
20161276
Science. 2000 Mar 17;287(5460):1960-4
10720314
Chem Rev. 2009 Sep;109(9):4439-86
19480390
Acc Chem Res. 2008 Jan;41(1):40-9
18159936
Angew Chem Int Ed Engl. 2006 Feb 27;45(10):1611-4
16470751
Angew Chem Int Ed Engl. 2008;47(31):5803-5
18613188
Inorg Chem. 2007 Jun 25;46(13):5149-51
17523635
J Am Chem Soc. 2009 Nov 18;131(45):16404-6
19856916
J Am Chem Soc. 2006 Sep 20;128(37):12056-7
16967941
Chem Rev. 2002 Jul;102(7):2477-95
12105933
J Org Chem. 2008 Sep 5;73(17):6686-90
18687000
J Am Chem Soc. 2007 Apr 18;129(15):4508-9
17378561
J Am Chem Soc. 2009 Aug 19;131(32):11350-2
19722648