Divergent and Chemoselective Transformations of Thioamides with Designed Carbene Equivalents
The reactions of thioamides with ortho‐nitro‐substituted iodonium ylides proceeded under mild conditions to give enaminones or thiazoles, depending on the iodonium ylide used. This protocol allowed the use of protic solvents, including aqueous solutions, and therefore coupling reactions with complex...
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Published in | Chemistry : a European journal Vol. 25; no. 44; pp. 10314 - 10318 |
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Main Authors | , , |
Format | Journal Article |
Language | English |
Published |
WEINHEIM
Wiley
06.08.2019
Wiley Subscription Services, Inc |
Subjects | |
Online Access | Get full text |
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Summary: | The reactions of thioamides with ortho‐nitro‐substituted iodonium ylides proceeded under mild conditions to give enaminones or thiazoles, depending on the iodonium ylide used. This protocol allowed the use of protic solvents, including aqueous solutions, and therefore coupling reactions with complex molecules such as peptides or steroids were possible. A mild and efficient method for the synthesis of various iodonium ylides was established. DFT calculations suggested that the halogen bonding between a thioamide and iodonium ylide was important in this chemoselective coupling reaction. The potential use of enaminones conjugated with pharmaceuticals as prodrugs was also demonstrated.
Useful carbene equivalents: The reactions of thioamides with ortho‐nitro‐substituted iodonium ylides proceeded under mild conditions to give enaminones or thiazoles. This protocol allowed the use of protic solvents, including aqueous solutions, and therefore coupling reactions with complex molecules were possible. A mild and efficient method for the synthesis of various iodonium ylides was also established (see scheme). |
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Bibliography: | ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23 |
ISSN: | 0947-6539 1521-3765 |
DOI: | 10.1002/chem.201902699 |