113655-80-4

Upstream product

• 113655-69-9 4-(o-bromobenzyl)azetidin-2-one 
• 33588-64-6 ethyl 2-(1H-indol-2-yl)acetate 
• 64132-03-2 ethyl 2-(2,3-dihydro-1H-indole-2-yl)acetate 
• 3433-80-5 1-Bromo-2-bromomethyl-benzene 

Relevant academic research and scientific papers

Active-copper-promoted expeditious N-arylations in aqueous media under microwave irradiation

Active-copper-promoted mild and expeditious N-arylations of amines, amides, imides, and β-lactams with aryl halides under microwave irradiation conditions are reported. These reactions can be performed at 85-90 °C in aqueous media as well as under solvent-free conditions to give good yields. However, under solvent-free conditions, lower yields are obtained. Georg Thieme Verlag Stuttgart.

Benzocarbapenems from indoles

The 8,8a-dihydroazeto[1,2-a]indol-2(1H)-ones (benzocarbapenems) 1a, 16, 17, 22, 27, 35 and 36 have been prepared by cyclodehydration of the corresponding β-amino acids, these amino acids being obtained by reduction of the analogous 2-substituted or 2,7-disubstituted indoles. The hydroxy group of compound 36 is designed to mimic the carboxylic acid function of the carbapenems on the basis of molecular modelling. The azetidinones 1a and 27, which are unsubstituted at the methylene group of the four-membered ring, are unstable and highly susceptible to ring opening by nucleophiles but the compounds 22,35 and 36 with two methyl substituents at this position are much more stable. The carbonyl stretching frequency in the IR is close to 1770 cm-1 for all the azetidinones except the phenol 36 for which the absorption is at 1735 cm-1. An X-ray crystal structure of compound 36 is reported.

Benzocarbapenems from ethyl indole-2-acetate

The benzocarbapenem 1 has been prepared from ethyl indole-2-acetate by reduction, hydrolysis of the ester and cyclisation. The methyl substituted carbapenems 12, 13 and 14 have also been prepared. The hydrogenation of ethyl N-BOC-indole-2-propanoate 5 is diastereoselective.

Synthesis of Benzocarbacephem and Benzocarbapenem Derivatives by Copper-promoted Intramolecular Aromatic Substitution

Copper-mediated cyclisation of 4-azetidinones and 4-azetidinones proved to be a route to benzocarbacephem and benzocarbapenem derivatives respectively.The effect of functionalities present in the alkyl part of the ring to be formed was considered with regard to cyclisation efficiency and further chemical modifications.Conversion, into halide, of the diastereoisomeric mixture (4R,6S; 4S,6R; 4R,6R; and 4S,6S) of t-butyl 2-hydroxybenzocarbacephem-4'-carboxylate (14f) afforded either the chloride (17a) as racemic diastereoisomers or the fluoride (17c) as a single racemic diastereoisomer.The corresponding free carboxylic acids (18a, c) were designed as inactivators of beta-lactamases.