29910-92-7Relevant articles and documents
Functionalized 2'-carboxamidodeoxybenzoins by ring opening of 3-aryl-1H-isochromen-1-ones with secondary amines
Shablykina, Olga V.,Moskvina, Viktoria S.,Ishchenko, Valentina V.,Valter, Eugenia B.,Khilya, Volodymir P.
, (2016)
[Figure not available: see fulltext.] An efficient approach based on pyrone ring opening in 3-arylisocoumarins in the presence of cyclic secondary amines was developed in order to prepare amides of deoxybenzoin-2'-carboxylic acids, diverse functionalized
Triflic acid mediated sequential cyclization of ortho-alkynylarylesters with ammonium acetate
Domaradzki, Maciej E.,Liu, Xiaochen,Ong, Jiye,Yu, Gyeongah,Zhang, Gan,Simantov, Ariel,Perl, Eliyahu,Chen, Yu
, (2020/08/03)
A triflic acid (TfOH) mediated sequential cyclization of ortho-alkynylarylesters and ammonium acetate (NH4OAc) was reported. The reaction took place via a Br?nsted acid-mediated intramolecular cyclization of ortho-alkynylarylesters followed by an ammonium acetate participated substitution reaction, forming isoquinolin-1-ones as the major products. Different from most of the known synthetic methods of isoquinolin-1-ones, no metal catalyst was required in the reported reaction. The regioisomers – isoindolin-1-ones were obtained together with isoquinolin-1-ones in a few cases. The intermediate compounds – isochromen-1-ones and isobenzofuran-1-ones were also isolated. The interconversion experiments showed that the regioisomers formed during the Br?nsted acid induced intramolecular cyclization of ortho-alkynylarylesters. A natural product – ruprechstyril was prepared in a moderate yield employing the new method.
Regioselective cyclization of 2-alkynylbenzoic acid in water for the synthesis of isocoumarin
Wang, Yan-Hua,Qiu, Guanyinsheng,Zhou, Hongwei,Xie, Wenlin,Liu, Jin-Biao
supporting information, p. 3850 - 3855 (2019/06/17)
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.
