141264-24-6Relevant articles and documents
A photochemical C=C cleavage process: Toward access to backbone N-formyl peptides
Ball, Zachary T.,Wang, Haopei
, p. 2932 - 2938 (2022/01/12)
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.
Acyl Halide Induced Cleavage of N-Acylated Aminals
Boehme, Horst,Raude, Edgar
, p. 3421 - 3429 (2007/10/02)
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.
