Isabella L. Karle

2 papers in the library · 33 citations · publishing 1969-1970

Papers

Photocyclizations of pharmacodynamic amines. V. Unusual rearrangements of the mescaline skeleton

Journal of the American Chemical Society September 1, 1970 Osamu Yonemitsu, Hideo Nakai, Yuichi Kanaoka et al. 20 citations

The mescaline skeleton undergoes unusual rearrangements during photocyclization reactions. Irradiation of certain mescaline derivatives leads to products formed through unexpected bond cleavages and recombinations, rather than simple cyclization. The structures of the photoproducts were determined by spectroscopic methods and X-ray crystallography. The rearrangements involve migration of the trimethoxyphenyl group and formation of new carbon-nitrogen bonds, producing heterocyclic compounds not previously accessible by other routes. These findings illustrate the complexity of photochemical transformations in pharmacologically relevant amines and provide new synthetic pathways to novel ring systems.

DOI: 10.1021/ja00722a025 Mescaline Skeleton computer programming Stereochemistry Radical photochemical reactions

Photocyclizations of pharmacodynamic amines. III. Three-dimensional structure of 7-hydroxy-1,9,10-trimethoxy-4-azabicyclo[5.2.2]undeca-8,10-dien-3-one from mescaline

Journal of the American Chemical Society July 1, 1969 Osamu Yonemitsu, Hideo Nakai, Yuichi Kanaoka et al. 13 citations

The three-dimensional structure of a photocyclization product derived from mescaline, 7-hydroxy-1,9,10-trimethoxy-4-azabicyclo[5.2.2]undeca-8,10-dien-3-one, was determined by X-ray crystallography. The molecule contains a bicyclic ring system with an azabicyclo[5.2.2]undecane framework, including a ketone and hydroxyl group, and three methoxy substituents. The configuration confirms the stereochemistry resulting from the photochemical reaction of mescaline, a pharmacodynamic amine. This structural elucidation provides insight into the reaction pathway and the three-dimensional arrangement of atoms in the product.

DOI: 10.1021/ja01044a071 Mescaline Pharmacodynamics Stereochemistry Computational chemistry +1