- A photochemical C=C cleavage process: Toward access to backbone N-formyl peptides
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Photo-responsive modifications and photo-uncaging concepts are useful for spatiotemporal control of peptides structure and function. While side chain photo-responsive modifications are relatively common, access to photo-responsive modifications of backbone N-H bonds is quite limited. This letter describes a new photocleavage pathway, affording N-formyl amides from vinylogous nitroaryl precursors under physiologically relevant conditions via a formal oxidative C=C cleavage. The N-formyl amide products have unique properties and reactivity, but are difficult or impossible to access by traditional synthetic approaches.
- Ball, Zachary T.,Wang, Haopei
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p. 2932 - 2938
(2022/01/12)
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- Acyl iodides in organic synthesis. Reaction of acyl iodides with N,N-dimethyl carboxylic acid amides
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Acyl iodides RCOI (R = Me, Ph) reacted with N,N-dimethylformamide and N,N-dimethylacetamide Me2NC(=O)R' (R' = H, Me) along two concurrent pathways involving transacylation and cleavage of the Me-N bond. The first pathway leads to the formation of acyl group exchange products, and the second, to the corresponding imides R'CON(Me)COR.
- Voronkov,Tsyrendorzhieva,Rakhlin
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experimental part
p. 1476 - 1478
(2011/03/18)
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- Acyl Halide Induced Cleavage of N-Acylated Aminals
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Acyl halides attack N-acylated aminals 6 at the amine nitrogen as well as at the carboxamide group to form either N-halomethyl carboxamides 5 besides N,N-dialkyl carboxamides 11, or diacylamines 12 besides N,N-dialkylmethaneiminium halides 4.Depending on the variation of the substituents on both heteroatoms the cleavage may be directed to follow only one or the other pathway.Of highly synthetic interest is the broadly applicable preparation of methaneiminium salts 4 having bulky substituents on nitrogen by means of cleavage of the corresponding N,N-dialkyl-N'-formyl-N'-methylmethanediamines 6.
- Boehme, Horst,Raude, Edgar
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p. 3421 - 3429
(2007/10/02)
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