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Title: Einhorn reaction for the synthesis of aromatic building blocks for macrocyclization

Journal Article · · Journal of Organic Chemistry
DOI:https://doi.org/10.1021/jo9617070· OSTI ID:539171
; ;  [1]
  1. Brigham Young Univ., Provo, UT (United States); and others

The present study concerns the synthesis of bis({alpha}-haloacetamidomethyl) and benzyldiamine sythons 1-3 (Scheme 1) through amidomethylation and their application for the preparation of benzoazamacroheterocycles. These synthons are useful as rigid building blocks containing the chromophoric NO{sub 2} group. The methoxy function could be converted to the phenolic OH after ring closure, providing a proton-ionizable group in the macrocyclic cavity. The authors show three synthetic routes to prepare benzoazamacrocycles using synthons 1-3. 11 refs.

DOE Contract Number:
FG02-86ER13463
OSTI ID:
539171
Journal Information:
Journal of Organic Chemistry, Vol. 62, Issue 1; Other Information: PBD: 10 Jan 1997
Country of Publication:
United States
Language:
English