Issue in Honor of Prof. Vladimir I. Minkin ARKIVOC 2005 (vii) 72-81
Synthesis and structure of spirooxazines of the thieno[3,2b] pyrroline series
Valerii Z. Shirinian., Mikhail M. Krayushkin.*, Denis M. Nikalina, Alexey A. Shimkina, Lyudmila G. Vorontsovaa, and Zoya A. Starikovab
a N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky prosp., 47, 119991 Moscow, Russian Federation b A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 117813 Moscow, Russian Federation E-mail: mkray@mail.ioc.ac.ru
Dedicated to Professor Vladimir Minkin on his 70th birthday (received 02 Feb 05; accepted 18 Mar 05; published on the web 26 Mar 05)
Abstract
A series of spironaphthoxazines based on thieno[3,2-b]pyrroline derivatives were synthesized and their structures were studied by 1. NMR spectroscopy, mass spectrometry, and X-ray diffraction. Comparative analysis of the spatial structures of spirooxazines of the thieno[3,2b] pyrroline and indoline series was performed.
Keywords: Thieno[3,2-b]pyrroles, spirooxazines, Fischer reaction, thieno[3,2-b]pyrrolenines, Xray diffraction analysis, Fischer’s salt
Introduction
Organic photochromes are widely used in various fields of science and engineering, in particular, for the design of light filters, optically controlled molecular switches, photochromic organic media for optical information recording and processing, etc. Among various classes of photochromic substances, spirooxazines (SPO) are distinguished by high sensitivity and resolving power.1-4 The vast majority of known spirooxazines belong to the indoline series. It appeared of interest to prepare close analogs of these compounds containing the thieno[3,2b] pyrrole heterocyclic systems instead of the indole system. Similar replacement of the benzene ring by a less aromatic and electron rich thiophene ring in photochromic compounds can give rise to new valuable properties and induce further chemical modification of products.
ISSN 1424-6376 Page 72 ©ARKAT USA, Inc
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