ORGN 675 |
SES/rearrangement cascade: Novel C-2/C-3 rearrangements of indoles
| Parag V. Jog, Dallas K. Bates, and Mary E. Eggers. Department of Chemistry, Michigan Technological University, 1400 Townsend Drive, Houghton, MI 49931 |
| Sulfoxide Electrophilic Substitution (SES) is a process in which a sulfoxide under Pummerer Reaction conditions (typically TFAA, CH2Cl2, 0 oC) reacts with an electron rich (hetero)aromatic ring to form a sulfonium salt. We have exploited this process previously in one-pot SES/displacement and SES/ring-opening cascades to prepare a variety of novel N,S-heterocyclic systems. We now report the first examples of a new cascade: SES/rearrangement. Thus, isomeric sulfoxides 1 and 3 both provide the same product [2, 5,7-dimethyl-5H-indolo[3,2-b][1,5]benzothiazepin-6(7H)-one] in excellent yields upon treatment with TFAA. 
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New Reactions, Methodology, Heterocycles, Aromatics
8:00 PM-10:00 PM, Wednesday, August 25, 2004 Pennsylvania Convention Center -- Hall D, Poster
Sci-Mix
8:00 PM-10:00 PM, Monday, August 23, 2004 Pennsylvania Convention Center -- Hall D, Sci-Mix
Division of Organic Chemistry
The 228th ACS National Meeting, in Philadelphia, PA, August 22-26, 2004
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