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New Luminescent Materials Based on a Steroid Molecule
Author(s) -
Wagner Kerstin,
Weiss Dieter,
Beckert Rainer
Publication year - 2000
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/1099-0690(200009)2000:17<3001::aid-ejoc3001>3.0.co;2-d
Subject(s) - steroid , chemistry , oxazoline , ring (chemistry) , substructure , molecule , luminescence , combinatorial chemistry , diazo , stereochemistry , organic chemistry , materials science , optoelectronics , structural engineering , engineering , catalysis , biochemistry , hormone
An efficient way to synthesize new steroid derivatives substituted in the A ring is described; based on a new route to stable diazo steroid 3‐diazoandrosta‐1,4‐dien‐17‐one ( 4 ). Using the Barton−Kellogg olefination, it is possible to combine the steroid molecule with a heterocyclic substructure: the oxazoline ring system. Unlike the starting material, the resulting oxazinylidene products 2 are luminescence dyes with high quantum yields, and possess Stokes shifts of about 100 nm. The described synthetic method opens the way for the development of new diagnostic and pharmaceutical materials containing a steroidal substructure.