210558-20-6

Upstream product

• 89-51-0 Homophthalic acid 
• 609-65-4 o-chlorobenzoyl chloride 
• 1864-94-4 phenyl formate 
• 51050-54-5 3-Chloroisocoumarin 
• 3900-89-8 2-Chlorobenzeneboronic acid 
• 118-91-2 ortho-chlorobenzoic acid 
• 210558-22-8 2-[2-(2-Chloro-phenyl)-2-oxo-ethyl]-benzoic acid 
• 88-67-5 2-Iodobenzoic acid 
• 873-31-4 2-chlorophenylacetylene 

Downstream Products

• 210558-22-8 2-[2-(2-Chloro-phenyl)-2-oxo-ethyl]-benzoic acid 

Relevant academic research and scientific papers

Regioselective cyclization of 2-alkynylbenzoic acid in water for the synthesis of isocoumarin

In this work, a regioselective synthesis of isocoumarins from 2-alkynylbenzoic acid is reported. The transformations proceed smoothly with good yields in water via a metal-free radical pathway. When catalytic TBAB is employed, the reaction provides various isocoumarin derivatives according to the structures of the corresponding precursors. It is believed that TBAB serves as a phase transfer catalyst and radical initiator in the reaction. Compared to previous methodologies, the synthetic procedure reported herein provides a more environmentally benign route for the synthesis of isocoumarins.

Ag2O nanoparticle-catalyzed substrate-controlled regioselectivities: direct access to 3-ylidenephthalides and isocoumarins

Herein, we disclose the first example of an efficient, silver oxide nanoparticle-catalyzed, direct regioselective synthesis of 3-ylidenephthalides 11-16 and isocoumarins 17-20via sonogashira type coupling followed by substrate-controlled 5-exo-dig or 6-endo-dig cyclization reaction, respectively. This one pot coupling involves reaction of substituted 2-halobenzoic acid with meta/para-substituted and ortho-substituted terminal alkynes, which proceeded in a regioselective manner resulting in the formation of 3-ylidenephthalides or isocoumarins, respectively, in excellent yields (up to 95%) with complete Z-selectivity. This protocol features relatively broad substrate scope, mild conditions, operational simplicity, and is favourable with aromatic/alicyclic terminal alkynes. The competition experiments and gram-scale synthesis further highlight the importance and versatility of the methodology. The proposed mechanistic pathways illustrate that the regioselectivity is substantially being controlled by the substituent(s) present on the acetylenic phenyl ring.

Palladium-catalyzed carbonylative synthesis of isocoumarins and phthalides by using phenyl formate as a carbon monoxide source

A simple and efficient palladium-catalyzed intramolecular carbonylative synthesis of isocoumarins and phthalides from the easily available starting materials by employing phenyl formate as a CO surrogate has been achieved. The approach affords target compounds in good to excellent yields with the advantages of lower toxicity, milder conditions, easy operation and wide functional group tolerance.

Palladium catalyzed Suzuki Miyaura cross coupling of 3-chloroisochromen-1-one: Synthesis of glomellin and reticulol analogues

A facile protocol has been developed for a series of 3-substituted isochromen-1-ones utilizing Suzuki coupling strategy. The reaction of 3-chloroisochromen-1one, 1 with different boronic acids utilizing PdCl2(PPh3)2-Ruphos catalytic system gave diversified 3-substituted isochromen-1-ones in excellent yields. The methodology has been utilized in the synthesis of glomellin and reticulol analogues.

New method for the synthesis of lactones via nickel-catalyzed isocyanides insertion

A novel nickel catalyst for the reaction of tert-butyl isocyanide insertion was discovered. In this approach, 1,2-bis(diphenylphosphino)ethane (L3) serves as an efficient ligand, thereby allowing the preparation of lactones from (o-bromophenyl)phenylethanone derivatives. It is noteworthy that this is the first example of nickel acting as a metal catalyst in the reactions of tert-butyl isocyanide insertion. The significance of this methodology may draw many chemists attention in the field of isocyanide-incorporating reactions. [Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications for the following free supplemental resource(s): Full experimental and spectral details.]

Palladium-catalyzed synthesis of isocoumarins and phthalides via tert -butyl isocyanide insertion

A novel and highly efficient strategy for the synthesis of isocoumarins and phthalides through a palladium(0)-catalyzed reaction incorporating tert-butyl isocyanide has been developed. This process, providing one of the simplest methods for the synthesis of this class of valuable lactones, involves two steps including cyclization reaction and simple acid hydrolysis. The methodology is tolerant of a wide range of substrates and applicable to library synthesis.

3-Substituted isocoumarins as thymidine phosphorylase inhibitors

3-Substituted isocoumarins 1-19 were synthesized and evaluated for their thymidine phosphorylase inhibitory activity. Eight (8) compounds exhibited a varying degree of inhibitory activity towards thymidine phosphorylase from E. coli with IC50 values between 61- 402 μM. The activities were compared with the standard 7-deazaxanthine (IC50 = 39.28 ± 0.76 μM).

Synthesis of some new 3-(chlorophenyl)isocoumarins and their conversion to 3,4-dihydro derivatives

Condensation of homophthalic acid 4 with chlorobenzoyl chlorides 5a-c yields 3-(chlorophenyl)isocoumarins 6a-c which on alkaline hydrolysis give the keto-acids 7a-c. (dl)-3-(Chlorophenyl)-3,4-dihydroisocoumarins 10a-c have been obtained by the reduction of 7a-c to racemic hydroxyacids 9a-c followed by cyclodehydration using acetic anhydride.