Synthesis of β-hydroxyacetamides from unactivated ethyl acetates under base-free conditions and microwave irradiation

Synthesis and characterization of ethyl benzotriazolyl acrylate-based D–π–A fluorophores for live cell-based imaging applications

“…We suspected that the low yield could be strongly inuenced by the lower reactivity of the 4-(diphenylamino)benzaldehyde; therefore, we decided to carry out the reaction under microwave irradiation, in accordance with our previous studies. 39,40 We found that at 100 C for 80 min, the yield of 6c increased from 20% to 56%. The reaction of benzotriazole 4 with aromatic aldehydes 5a and 5d afforded ethyl benzotriazolyl acrylates 7a and 7d with yields of 61% and 71%.…”

First practical synthesis of novel 1‐phosphonylated pyrrolo[1,2‐a]pyrazine derivatives

“…The synthetic sequence established in the route A began with the reaction of 2‐formyl‐1 H ‐pyrrole with benzylamine and dimethyl phosphite at 50°C in the presence of 10 mol% of phenylboronic acid as catalyst under solvent‐free conditions, obtaining the α‐aminophosphonate 8 in 83% yield after 2.0 hours,[15b] which was treated with bromoacetyl bromide and K 2 CO 3 in a dichloromethane:water mixture, to obtain the corresponding N ‐bromoacetamide 5 in 78% yield . Finally, the treatment of the N ‐bromoacetamide 5 with potassium iodide and K 2 CO 3 in acetone at reflux for 5.0 hours, afforded the α‐aminophosphonate with the pyrrolo[1,2‐ a ]pyrazine core 9a in 85% yield (Scheme ).…”

Practical synthesis of novel phosphonopeptides containing AibP

“…With the quaternary α ‐aminophosphonate 6 in hand, in the next step, we turned our attention on the acylation of the α ‐amino group to obtain the 1‐( N ‐bromoacetyl‐amino)phosphonate 7 , considering that these compounds represent a useful synthetic intermediate, exhibiting a broad potential of a number of subsequent functionalizations. Thus, the quaternary α ‐aminophosphonate 6 was treated with bromoacetyl bromide and K 2 CO 3 in a CH 2 Cl 2 :H 2 O mixture at 0 °C , obtaining the corresponding N ‐bromoacetamide 7 in 82% yield (Scheme ).…”