A practical and efficient two-step synthesis of N-substituted isoindolin-1-ones was developed. The one-pot reaction of 2-formylbenzoic acid with amines and dimethyl phosphite proceeds in short time either with conventional heating or microwave irradiation under catalyst-free conditions to afford the corresponding Nsubstituted dimethyl 3-oxoisoindolin-1-ylphosphonates in good yield which, by means of a dephosphonylation reaction with lithium aluminum hydride, give the target N-substituted isoindolin-1-ones in moderate to good yield.Isoindolin-1-ones (2,3-dihydro-1H-isoindol-1-ones) have gained considerable attention recently due to their fascinating properties and potential applications in many fields, especially in biology and medicinal science. 1 The interest in these heterocyclic compounds stems mainly from their diverse biological activities. For example, isoindolin-1-ones 1-3 ( Figure 1) have been tested as antimicrobial agents, 2 while indoprofen (4) has been shown to have anti-inflammatory activity 3,4 and deoxythalidomide (5) is an inhibitor of tumor necrosis factor production. 5 Additionally, the isoindolin-1-one skeleton is a key intermediate for the synthesis of many naturally occurring bioactive compounds. 6 Figure 1Consequently, the chemistry of isoindolinones has attracted much attention, and a number of synthetic strategies have been developed over the past few years including the reduction of phthalimides, 7 the condensation of anilines with o-phthalaldehydes, 8 amination and lactamization of 2-carbomethoxybenzaldehyde, 6h,9 palladium(0)-catalyzed carbonylation-amination, 10 synthesis from isocyanates 11 and base-induced aryne-mediated cyclization of o-halo-N-(phosphinylmethyl)benzamide derivatives; 12,13 however, despite their potential utility, these procedures typically suffer from one or more disadvantages, such as the use of harsh conditions or tedious multisteps which are necessary for these syntheses. Thus, there is still a need to develop versatile and flexible methods for the synthesis of isoindolin-1-ones. In this context, herein we describe an efficient method for the synthesis of N-substituted isoindolin-1-ones. Our synthetic strategy is based upon a onepot reaction of 2-formylbenzoic acid with alkyl-or arylamines and dimethyl phosphite using conventional heating or microwave irradiation under catalyst-free conditions, 14 followed by a dephosphonylation reaction.We have recently developed 15 an efficient and highly diastereoselective method for the synthesis of 3-oxoisoindolin-1-ylphosphonate 7a by a three-component, one-pot reaction of 2-formylbenzoic acid (6), (S)-a-methylbenzylamine and dimethyl phosphite under catalyst-and solvent-free conditions (Table 1, entry 1). To establish the generality of this three-component, one-pot process we carried out the reaction of 2-formylbenzoic acid (6) with either alkyl-or arylamines and dimethyl phosphite. Thus, the reaction of 2-formylbenzoic acid (6) with tert-butylamine or benzhydrylamine and dimethyl phosphite at 80°C under catalyst-and sol...

Uncatalyzed one-pot, three-component reactions of aldehydes, chiral α-methylamines, and dimethyl phosphite under solvent-free conditions were used for the diastereoselective synthesis of α-amino phosphonates. The reactions proceeded

The crystal structure of enanti­opure (3aS,4S,5R,7aR)-2,2,7-trimethyl-3a,4,5,7a- tetra­hydro-1,3-benzodioxole-4,5-diol shows that the absolute configuration determined from the synthesis pathway agrees with that determined by X-ray analysis.

A simple, efficient and general method has been developed for the high diastereoselective synthesis of α-aminophosphonates through “one-pot” three-component reaction of alkyl and aryl aldehydes with (S)-α-methylbenzylamine or (S)-3,3-dimethyl-2-butylamine and dimethyl phosphite (Kabachnik-Fields reaction), which proceeds in short time using microwave irradiation under solvent and catalyst free-conditions. This method could be useful in the large-scale synthesis of α-aminophosphonates in short reaction time

Within food wastes, including edible and inedible parts, fat biomasses represent a significant portion, often uneconomically used or improperly disposed causing pollution issues. Interesting perspectives for their management and valorization could be opened by conversion of fatty acids (FAs), which are their main constituents, into α-hydroxy FAs (α-HFAs), fine chemicals of great, but largely untapped potential, possibly due to current poor availability. Here, a simple and efficient procedure is reported to α-chlorinate FAs with trichloroisocyanuric acid (TCCA), a green halogenating agent, under solvent-free conditions and to directly convert the resultant α-chloro FAs, without previous purification, into α-HFAs. The procedure was applied to stearic, palmitic, and myristic acid and, with analogous success, to their mixture, ad hoc created to simulate a FAs mixture obtainable from a fat biomass.