Propellane derivates and synthesis
Disclosed herein are compounds of the general Formula (I), and methods of synthesizing substituted bicyclo[1.1.1 jpentanes. The synthetic methods described herein use a [1.1.1]propellane, a Group VIII transition metal compound, a hydride source and a reagent that can contribute a substituent to form a substituted bicyclo[1.1.1]pentane, such as a compound of the general Formula (I).
1. A compound having the structure of Formula (I):
wherein:
R 1 is —N 3 , —SCN, —NO, —C(═NOR 2 )(CN), —CH(═NOR 2 ), CH(CO 2 H)(NHBoc), —CH(CO 2 H)(NH 2 ), an optionally substituted cycloalkynyl, an optionally substituted heteroaryl(C 1-6 alkyl), an optionally substituted heterocyclyl(C 1-6 alkyl), an optionally substituted aminoalkyl or an optionally substituted haloalkoxy; and
R 2 is (C 1 to C 10 ) alkoxy, an optionally substituted C 1-30 alkyl, an optionally substituted alkenyl, an optionally substituted alkynyl, an optionally substituted cycloalkyl, an optionally substituted cycloalkenyl, an optionally substituted cycloalkynyl, an optionally substituted aryl, an optionally substituted heteroaryl, an optionally substituted heterocyclyl, an optionally substituted aryl(alkyl), an optionally substituted heteroaryl(alkyl), an optionally substituted heterocyclyl(alkyl), an optionally substituted aminoalkyl or an optionally substituted alkylamino;
wherein an optionally substituted aminoalkyl is a NH 2 group connected, as a substituent, via a lower alkylene group; and
wherein the optionally substituted aminoalkyl is a straight-chained —CH 2 — tethering group, forming bonds to connect molecular fragments via its terminal carbon atoms and wherein the lower alkylene group can be substituted by replacing one or more hydrogen of the lower alkylene group or by substituting both hydrogens on the same carbon with a cycloalkyl group.
2. The compound of claim 1 , wherein the compound is
3. The compound of claim 1 , wherein R 1 is a substituted aminoalkyl.
4. The compound of claim 1 , wherein R 1 is an unsubstituted aminoalkyl.
5. The compound of claim 1 , wherein R 1 is H 2 N—(CH 2 )n-, wherein n is an integer in the range of 1 to 6.
6. The compound of claim 5 , wherein n is 1.
7. The compound of claim 5 , wherein n is 2.
8. The compound of claim 5 , wherein n is 3.
9. The compound of claim 5 , wherein n is 4.
10. The compound of claim 5 , wherein n is 5.
11. The compound of claim 1 , wherein the compound is
12. The compound of claim 1 , wherein the compound is
13. The compound of claim 1 , wherein the compound is