Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 86, Issue 21, Pages 15033-15044Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.1c01717
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Funding
- Ministry of Science and Technology, Taiwan [MOST 109-2113-M030-007]
- Instrumentation center, National Taiwan University [MOST 109-2731-M-002-001, MS000100]
- Department of Chemistry Master Student Fellowships
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Various N-(2-bromo-allyl) benzamides were used as starting materials for studying vinyl radical cyclization reactions, which produced beta-aryl-gamma-lactams without affecting the carbonyl group. The cascade radical reaction led to the synthesis of alpha,beta-unsaturated-beta-aryl-gamma-lactam derivatives, with the effects of substituents on the amino and aryl groups examined.
Various N-(2-bromo-allyl) benzamides were used as the starting materials to study vinyl radical cyclization reactions. The vinyl radicals underwent ipso-cyclization, fragmentation, and cyclization reactions to produce beta-aryl-gamma-lactams with the carbonyl group remaining intact. To further study this cascade radical reaction, vinyl radicals were generated by the addition of a tributyltin radical to alkyne moieties, followed by radical ipso-cyclization, fragmentation, cyclization, and beta-scission reactions with the production of a series of alpha,beta-unsaturated-beta-aryl-gamma-lactam derivatives. This new type of radical reaction was examined from the substituent effects on both the amino groups and the aryl groups. A bulky tert-butyl substituent on the amino group enhanced the formation of a Z-conformation of the benzamides and facilitated vinyl radical ipso-cyclization reactions. A synthetic method for preparing alpha,beta-unsaturated-beta-aryl-gamma-lactams from N-propargyl benzamides was developed.
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