Highly regioselective, electrophile induced cyclizations of 2-(prop-1-ynyl)benzamides
| Autor: | Beeraiah Baire, Bhavani Shankar Chinta, Kamala Prasad Vasikarla, Harikrishna Sanapa |
|---|---|
| Rok vydání: | 2018 |
| Předmět: |
chemistry.chemical_classification
Steric effects 010405 organic chemistry Organic Chemistry Substituent Alkyne Structural diversity Regioselectivity 010402 general chemistry 01 natural sciences Biochemistry Medicinal chemistry 0104 chemical sciences chemistry.chemical_compound chemistry Metal free Amide Electrophile Physical and Theoretical Chemistry |
| Zdroj: | Organic & Biomolecular Chemistry. 16:3947-3951 |
| ISSN: | 1477-0539 1477-0520 |
| Popis: | We report an electrophile promoted, highly regioselective (∼100%) synthesis of 5-membered haloimidiates from 2-(1-alkynyl)benzamides under metal free conditions. The steric bulk in association with neighbouring group assistance at the propargylic carbon of an alkyne has been employed as the dictating factor to achieve the regioselectivity. A very broad structural diversity has been observed for propargylic alcohols and acetates, and for amide functional groups. Control experiments supported the role of the steric bulk as well as neighbouring group assistance from the oxygen atom of the substituent for the observed high regioselectivity. |
| Databáze: | OpenAIRE |
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