Electronically activated strained alkynes

Patent metadata

Field	Value
Publication number	US-2018201593-A1
Application number	US-201815873984-A
Country	US
Kind code	A1
Filing date	Jan 18, 2018
Priority date	Jan 18, 2017
Publication date	Jul 19, 2018
Grant date	—

Abstract

Compounds of Formula I:

wherein:
R 1 and R 2 are hydrogen or C 1 to C 12 linear or branched alkyl; R 3 is hydrogen, C 1 to C 12 linear or branched alkyl, or nitrogen protecting groups; X is oxygen or nitrogen; and when X is oxygen, R 4 is absent; and when X is nitrogen, R 4 is C 1 to C 12 linear or branched alkyl or nitrogen protecting groups. The compounds are useful as reagents in 1,3-cycloaddition reactions.

First claim

What is claimed is:

1 . Compounds of Formula I:

wherein:
R 1 and R 2 are independently selected from hydrogen and C 1 to C 12 linear or branched alkyl;
R 3 is selected from hydrogen, C 1 to C 12 linear or branched alkyl, and nitrogen protecting groups;
X is oxygen or nitrogen;
when X is oxygen, R 4 is absent; and
when X is nitrogen, R 4 is selected from C 1 to C 12 linear or branched alkyl and nitrogen protecting groups.

2 . The compounds of claim 1 , wherein X is oxygen.

3 . The compounds of claim 1 , wherein X is nitrogen.

4 . The compounds of claim 3 , wherein R 4 is C 1 to C 12 linear or branched alkyl.

5 . The compounds of claim 3 , wherein R 4 a nitrogen protecting group.

6 . A compound of claim 1 , wherein one of R 1 or R 2 is C 1 to C 12 linear or branched alkyl.

7 . The compounds of claim 6 , wherein X is oxygen.

8 . The compounds of claim 6 , wherein X is nitrogen.

9 . The compounds of claim 8 , wherein R 4 is C 1 to C 12 linear or branched alkyl.

10 . The compounds of claim 8 , wherein R 4 a nitrogen protecting group.

11 . A compound of claim 1 , wherein R 1 and R 2 are C 1 to C 12 linear or branched alkyl.

12 . The compounds of claim 11 , wherein X is oxygen.

13 . The compounds of claim 11 , wherein X is nitrogen.

14 . The compounds of claim 13 , wherein R 4 is C 1 to C 12 linear or branched alkyl.

15 . The compounds of claim 13 , wherein R 4 a nitrogen protecting group.

16 . A compound of claim 1 , wherein one of R 1 or R 2 is C 1 to C 6 linear or branched alkyl.

17 . The compounds of claim 16 , wherein X is oxygen.

18 . The compounds of claim 16 , wherein X is nitrogen.

19 . The compounds of claim 18 , wherein R 4 is C 1 to C 12 linear or branched alkyl.

20 . The compounds of claim 18 , wherein R 4 a nitrogen protecting group.

21 . A compound of claim 1 , wherein R 1 and R 2 are C 1 to C 6 linear or branched alkyl.

22 . The compounds of claim 21 , wherein X is oxygen.

23 . The compounds of claim 21 , wherein X is nitrogen.

24 . The compounds of claim 23 , wherein R 4 is C 1 to C 12 linear or branched alkyl.

25 . The compounds of claim 23 , wherein R 4 a nitrogen protecting group.

26 . A method of forming chemical bonds, the method comprising reacting a first compound of Formula I:

wherein:
R 1 and R 2 are independently selected from hydrogen and C 1 to C 12 linear or branched alkyl;
R 3 is selected from hydrogen, C 1 to C 12 linear or branched alkyl, and nitrogen protecting groups;
X is oxygen or nitrogen;
when X is oxygen, R 4 is absent; and
when X is nitrogen, R 4 is selected from C 1 to C 12 linear or branched alkyl and nitrogen protecting groups;
with a second compound comprising a 1,3-dipole, in a 1,3-cycloaddition reaction.

Assignees

• Wisconsin Alumni Res Found

Inventors

• Schomaker Jennifer M
• Burke Eileen G

Classifications

• C07D291/02 Primary

  not condensed with other rings · CPC title

• C07D285/38

  Eight-membered rings · CPC title