An efficient, three-component synthesis of isoindolin-1-one-3-phosphonates under mild and solvent-free conditions (original) (raw)
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Tetrahedron-asymmetry, 2011
The one-pot three-component reaction of 2-formylbenzoic acid with (S)-and (R)-methylbenzylamine and dimethyl phosphite (Kabachnik-Fields reaction) proceeded in short reaction times under solvent and catalyst free-conditions to afford the corresponding (3R,1 0 S)-and (3S,1 0 R)-isoindolin-1-one-3-phosphonates 3, respectively, in good yield and with high diastereoselectivity (95:5 dr). The use of a solvent decreases the diastereoselectivity and slows the reaction rate. The reaction rate was also influenced by CO 2 H functionality through protonation of the imine intermediate. The absolute configuration at the new stereogenic center was determined by X-ray crystal analysis, and a mechanism was proposed to explain the high diastereoselectivity.
Molecules, 2020
A simple and efficient microwave (MW)-assisted method was elaborated for the catalyst-free synthesis of isoindolin-1-one-3-phosphonates by the three-component condensation of 2-formylbenzoic acid, aliphatic primary amines and various dialkyl phosphites. The batch and the continuous flow reactions were optimized in respect of the temperature, the reaction time and the molar ratio of the starting materials. To evaluate the potential of MW irradiation, comparative thermal experiments were also carried out. In order to obtain “real time” information about the condensation, the special Kabachnik–Fields reaction of 2-formylbenzoic acid, butylamine and diethyl phosphite was monitored by in situ FT-IR spectroscopy. The novel title compounds could be prepared in high yields at low temperature under a short reaction time. A suitable method could also be developed for the preparation of the isoindolin-1-one-3-phosphonates at a “few g” scale by using a continuous flow MW reactor.
Phosphono-substituted isoindolines and indoles from 2,3- and 2,4-benzoxazin-1-ones
Heteroatom Chemistry, 2004
Reactions of 2,3-benzoxazinone 1 and 2,4-benzoxazinone 2, with trialkyl phosphites 3a-c provide access to new phosphono-substituted isoindolines 6a-f and indoles 19a-e, respectively. Phosphonosubstituted 2,3-benzoxazines 5a-c were also obtained in the first reaction. Bisisoindolinylidene was, however, isolated in low yields when 1 was heated with triethyl or triisopropyl phosphite at 100 • C whereas at 170 • C 7 was obtained as the major product (∼53%). On the other hand, the reaction of 1 or 2 with dialkyl phosphonates 4a-c proceeded in the presence of aqueous solution of NaOH (5%) to give the respective alkylated product 14a-c or 20a-c. C 2003 Wiley Periodicals, Inc. Heteroatom Chem 15:77-84, 2004; Published online in Wiley InterScience (www.interscience.wiley.com).
Tetrahedron Letters, 2012
Practical and high stereoselective synthesis of 3-(arylmethylene)isoindolin-1-ones is reported. The synthetic method involves the preparation of dimethyl isoindolin-1-one-3-yl-phosphonates by a 'one-pot' three-component reaction of 2-formylbenzoic acid with 4-methoxybenzylamine or aminoacetaldehyde dimethyl acetal and dimethyl phosphite under solvent and catalyst free-conditions, followed by a Horner reaction with several aryl aldehydes.
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Simple and convenient procedures for the synthesis of derivatives of 2,3-dihydroinden-2-ylphosphonic acid are developed. The reaction strategies utilize both functionalization of the already existing 2,3-dihydroindene skeleton and an annulation reaction starting from readily available o-disubstituted benzene derivatives.
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Organophosphorus compounds play an important role in several fields of life; they have widespread use in organic and medicinal chemistry, as well as in agriculture and plastic industry. Over the last years, the chemistry of heterocyclic phosphonates has received an intensively growing interest. One of the most efficient tools for the preparation of these compounds is the synthesis via multicomponent reactions, which transformations meet several criteria of an “ideal synthesis”, such as high atom economy, fast and simple accomplishment, ability to save time and energy and being environment-friendly. The synthesis of isoindolin-1-one-3-phosphonate derivatives was studied by the microwave(MW)-assisted three-component reaction of 2‑formylbenzoic acid, aliphatic primary amines and various dialkyl phosphites. A suitable method was also developed for the preparation of the isoindolin-1-one-3-phosphonates at a “few g” scale by using a continuous flow MW reactor. (2-Amino-4H-chromen-4-yl)pho...
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Arkivoc, 2009
Bisphosphonates (BPs) are an important class of drugs used in the treatment of abnormal calcium metabolism diseases. The first syntheses of bisphosphonates derived from indazole, substituted at the N-1, N-2 and C-3 positions are reported. The 1-hydroxy-1,1-bisphosphonates were synthesized from the corresponding carboxylic acid or acyl chloride compounds, by two different methods. These BPs have a side chain with different lengths ((CH 2) n , n = 0-5) between the indazole ring and the bisphosphonate group.