4.8 Article

Intramolecular Schmidt Reaction of Acyl Chlorides with Alkyl Azides: Rapid Access to Fused Polycyclic Nitrogen-Containing Heterocycles via a Multistep One-Pot Transformation

Journal

ORGANIC LETTERS
Volume 14, Issue 22, Pages 5796-5799

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ol302890a

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Funding

  1. National Natural Science Foundation of China [21262024]
  2. Key Project of Chinese Ministry of Education [211193]
  3. 100 Talents Program of Ningxia
  4. Natural Science Foundation of Ningxia [NZ1043, NZ1165]
  5. National Basic Research Program 973 of China [2010CB534916]
  6. 211 Project in Ningxia University [ndzr09-1]

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The first intramolecular Schmidt reaction of acyl chlorides with alkyl azides has been developed. In this one-pot conversion, an omega-azido hydrocinnamic acid is converted to a tricyclic lactam. The most important feature of the process is the efficiency in bond formation (one bond broken and three new bonds created) and ring construction (two new rings formed).

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