Journal
TETRAHEDRON LETTERS
Volume 91, Issue -, Pages -Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2022.153637
Keywords
2-Oxazoline; One-pot synthesis; Microwave-assisted synthesis; Isocyanate; Retention of configuration
Categories
Funding
- National Natural Science Foundation of China [21774031, 21861162010, 31800801]
- Program of Shanghai Academic/Technology Research Leader [20XD1421400]
- Natural Science Foundation of Shanghai [18ZR1410300]
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We have developed a facile one-pot synthesis method for 2-oxazolines. This method can tolerate a wide range of functional groups under mild reaction conditions and provide diverse 2-oxazoline products with good yields. The chirality of the isocyanate at position 1 can be preserved, and microwave-assisted synthesis can further enhance the reaction yield and reduce the reaction time. This method is of great significance for the synthesis of 2-oxazoline-derived polymers and materials.
We developed a facile one-pot synthesis of 2-oxazolines from carboxylic acid and 2-chloroethyl isocyanate, involving amide bond formation and a following intramolecular cyclization using 4-dimethylaminopyridine as the catalyst. A large variety of functional groups are well tolerated by the mild reaction conditions to afford diverse 2-oxazolines in good to excellent yields. This reaction will keep the chirality of the isocyanate at position 1, the R-2 substituted carbon. Microwave-assisted synthesis can further enhance the reaction yield and reduce the reaction time to <5 min. This method facilities the synthesis of 2-oxazolines for diverse applications, such as 2-oxazoline derived polymers and materials. (C) 2022 Elsevier Ltd. All rights reserved.
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