Alkynes and methods of reacting alkynes with 1,3-dipole-functional compounds
AssigneeUniversity of Georgia Research Foundation, Inc.
InventorsGeert-Jan Boons, Jun Guo, Xinghai Ning, Margaretha Wolfert
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Abstract
1,3-Dipole-functional compounds (e.g., azide functional compounds) can be reacted with certain alkynes in a cyclization reaction to form heterocyclic compounds. Useful alkynes (e.g., strained, cyclic alkynes) and methods of making such alkynes are also disclosed. The reaction of 1,3-dipole-functional compounds with alkynes can be used for a wide variety of applications including the immobilization of biomolecules on a substrate.
Claims22
1-19. (canceled)
A compound of the formula:
- wherein:
- each R1 is independently selected from the group consisting of hydrogen, halogen, hydroxy, alkoxy, nitrate, nitrite, sulfate, and a C1-C10 organic group;
- each R2 is independently selected from the group consisting of hydrogen, halogen, hydroxy, alkoxy, nitrate, nitrite, sulfate, and a C1-C10 organic group;
- X represents C═O, C═N—OR3, C═N—NR3R4, CHOR3, or CHNHR3;
- each R3 and R4 independently represents hydrogen or an organic group;
- and
- R8 represents an organic group.
A compound of the formula:
- wherein:
- each R1 is independently selected from the group consisting of hydrogen, halogen, hydroxy, alkoxy, nitrate, nitrite, sulfate, and a C1-C10 organic group;
- each R2 is independently selected from the group consisting of hydrogen, halogen, hydroxy, alkoxy, nitrate, nitrite, sulfate, and a C1-C10 organic group;
- X represents C═O, C═N—OR3, C═N—NR3R4, CHOR3, or CHNHR3;
- and
- each R3, R4, and R10 independently represents hydrogen or an organic group, with the proviso that at least one R10 represents an organic group.
A compound of the formula:
- wherein:
- each R1 is independently selected from the group consisting of hydrogen, halogen, hydroxy, alkoxy, nitrate, nitrite, sulfate, and a C1-C10 organic group;
- each R2 is independently selected from the group consisting of hydrogen, halogen, hydroxy, alkoxy, nitrate, nitrite, sulfate, and a C1-C10 organic group;
- X represents C═O, C═N—OR3, C═N—NR3R4, CHOR3, or CHNHR3;
- and
- each R3, R4, and R10 independently represents hydrogen or an organic group, with the proviso that at least one R10 represents an organic group.
A method of preparing a heterocyclic compound, the method comprising:
- combining at least one alkyne with at least one 1,3-dipole-functional compound selected from the group consisting of an azide-functional compound, a nitrile oxide-functional compound, a nitrone-functional compound, an azoxy-functional compound, an acyl diazo-functional compound, and combinations thereof;
- and
- allowing the at least one 1,3-dipole-functional compound and the at least one alkyne to react under conditions effective to form the heterocyclic compound;
- wherein the alkyne is of the formula:
- wherein:
- each R1 is independently selected from the group consisting of hydrogen, halogen, hydroxy, alkoxy, nitrate, nitrite, sulfate, and a C1-C10 organic group;
- each R2 is independently selected from the group consisting of hydrogen, halogen, hydroxy, alkoxy, nitrate, nitrite, sulfate, and a C1-C10 organic group;
- X represents C═O, C═N—OR3, C═N—NR3R4, CHOR3, or CHNHR3;
- and
- each R3 and R4 independently represents hydrogen or an organic group.
A compound of the formula:
- wherein:
- each R1 is independently selected from the group consisting of hydrogen, halogen, hydroxy, alkoxy, nitrate, nitrite, sulfate, and a C1-C10 organic group;
- each R2 is independently selected from the group consisting of hydrogen, halogen, hydroxy, alkoxy, nitrate, nitrite, sulfate, and a C1-C10 organic group;
- X represents C═N—OR3, C═N—NR3R4, CHOR3, or CHNHR3;
- R3 represents a polymeric group, a copolymeric group, or an organic group attached to a nanoparticle;
- R4 represents hydrogen or an organic group;
- and
- R8 represents a biomolecule.
Dependencies are inferred from the claim text.