Abstract
A facile, one-pot procedure for the conversion of readily accessible acyl hydrazides into N-acyl carbamates.
Highlights
View Article OnlineThe use of 1.5 eq of ethyl bromoacetate and 3 eq of NaH was trialled at room temperature (Table 1, entry 1)
We report the one-pot transformation of readily synthesised/ accessed acyl hydrazides into Nacyl carbamates via an alkylation-elimination reaction sequence
We focus on developing a new method to form acyl carbamates from acyl hydrazides via rupture of the N–N bond in a one-pot alkylation-E1cB elimination procedure (Fig. 1)
Summary
The use of 1.5 eq of ethyl bromoacetate and 3 eq of NaH was trialled at room temperature (Table 1, entry 1) These conditions resulted in the formation of several entities: desired acyl carbamate 3a; alkylated-hydrazine intermediate 4a; trans-esteri ed acyl carbamate 3b; and over-alkylated product 5. To limit over-alkylation, the reaction was repeated with 1.1 eq of ethyl bromoacetate (Table 1, entry 2); this completely suppressed formation of over-alkylated product 5 This lowered the yield of trans-esteri ed acyl carbamate 3b; suggesting that the ethoxide, which is likely to facilitate the trans-esteri cation
Sign-in/Register to view highlights & summary Sign-in/Register to access full text options 
Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Schedule a callDisclaimer: All third-party content on this website/platform is and will remain the property of their respective owners and is provided on "as is" basis without any warranties, express or implied. Use of third-party content does not indicate any affiliation, sponsorship with or endorsement by them. Any references to third-party content is to identify the corresponding services and shall be considered fair use under The CopyrightLaw.
