Iodine(III)-Mediated Ring Contraction Reactions: Synthesis of Oxygen- and Nitrogen-Substituted Indanes
摘要:
The synthesis of oxygen-and nitrogen-substituted indanes was successfully performed by iodine(III)-mediated ring contraction of 1,2-dihydronaphthalenes. Acetoxy and benzoyloxy alkenes afforded indanes in 60-71% yield, irrespective of their position on aromatic ring. Similarly, the nitrogen containing substrates protected with 9-fluorenylmethyloxycarbonyl (Fmoc) and benzoyl (Bz) groups smoothly undergoes ring contraction giving indanes in 64-77% yield. The tosyl-protected substrate resulted only in addition products.
Iodine(III)-Mediated Ring Contraction Reactions: Synthesis of Oxygen- and Nitrogen-Substituted Indanes
摘要:
The synthesis of oxygen-and nitrogen-substituted indanes was successfully performed by iodine(III)-mediated ring contraction of 1,2-dihydronaphthalenes. Acetoxy and benzoyloxy alkenes afforded indanes in 60-71% yield, irrespective of their position on aromatic ring. Similarly, the nitrogen containing substrates protected with 9-fluorenylmethyloxycarbonyl (Fmoc) and benzoyl (Bz) groups smoothly undergoes ring contraction giving indanes in 64-77% yield. The tosyl-protected substrate resulted only in addition products.
A compound having Formula I
R
1
-Z-R
2
Formula I
wherein R
1
is an optionally substituted phenyl ring; R
2
is or comprises an optionally substituted-aromatic ring; and Z is -X-Y-L- or -Y-X-L- wherein either X is selected from —S(═O)(═O)— and —C(═O)—, and Y is —NR
3
—; or X is selected from —S(═O)(═O)— and —S—, and Y is —C(R
4
)(R
5
)—; L is an optional linker; and R
3
, R
4
and R
5
are each independently selected from H and hydrocarbyl; and wherein when R
2
comprises the following structural moiety
wherein Q is an atom selected from the group consisting of S, O, N and C; the compound is selected from compounds of the formulae R
1
C(═O)—NR
3
-L-R
2
; R
1
—S(═O)(═O)—C(R
4
)(R
5
)-L-R
2
; R
1
—S—C(R
4
)(R
5
)-L-R
2
; R
1
—NR
3
—S(═O)(═O)-L-R
2
; R
1
—NR
3
—C(═O)-L-R
2
; R
1
—C(R
4
)(R
5
)—S(═O)(═O)-L-R
2
; and R
1
—C(R
4
)(R
5
)—S-L-R
2
.
Iodine(III)-Mediated Ring Contraction Reactions: Synthesis of Oxygen- and Nitrogen-Substituted Indanes
作者:Anees Ahmad、Luiz F. Silva Júnior
DOI:10.5935/0103-5053.20160065
日期:——
The synthesis of oxygen-and nitrogen-substituted indanes was successfully performed by iodine(III)-mediated ring contraction of 1,2-dihydronaphthalenes. Acetoxy and benzoyloxy alkenes afforded indanes in 60-71% yield, irrespective of their position on aromatic ring. Similarly, the nitrogen containing substrates protected with 9-fluorenylmethyloxycarbonyl (Fmoc) and benzoyl (Bz) groups smoothly undergoes ring contraction giving indanes in 64-77% yield. The tosyl-protected substrate resulted only in addition products.