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Selenium‐Containing Heterocycles From Isoselenocyanates: Synthesis of1,3‐Selenazolidine and Perhydro‐1,3‐selenazine Derivatives

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TLDR
In this article, the structure of 1,3-selenazolidines and perhydro-1, 3-thiazines were established by X-ray crystallography.
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This article is published in European Journal of Organic Chemistry.The article was published on 2005-07-01 and is currently open access. It has received 43 citations till now. The article focuses on the topics: Triethylamine & Aryl.

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Journal ArticleDOI

Isoselenocyanates: a powerful tool for the synthesis of selenium-containing heterocycles.

TL;DR: In this review the recent advances in the development of synthesis methods for selenium-containing heterocycles from isoselenocyanates are presented and discussed.
Journal ArticleDOI

Recent advances in the chemistry of selenium-containing heterocycles: Five-membered ring systems

TL;DR: A comprehensive survey of the recent advances in the methods of construction of five membered ring systems containing selenium over the period from the year 2000 to the year 2015 can be found in this article.
Journal ArticleDOI

Base-promoted cascade reaction of isocyanides, selenium and amines: a practical approach to 2-aminobenzo[d][1,3]selenazines under metal-free conditions

TL;DR: In this article, a base mediated multicomponent reaction of isocyanides, selenium and amines under metal-free conditions is reported. And a series of selenazine derivatives are observed in moderate to excellent yields.
Journal ArticleDOI

Isoselenocyanates as Building Blocks for Selenium-Containing Heterocycles

TL;DR: Isoselenocyanates can be used either as reactive intermediates or as relatively stable and storable starting materials for the preparation of selenaheterocycles or heterocyclic selones as discussed by the authors.
Journal ArticleDOI

Selenium-containing heterocycles from isoselenocyanates: synthesis of 2-methylidene-1,3-selenazolidine derivatives

TL;DR: In this paper, a method for the synthesis of isoselenocyanates, malonitrile or 2-cyanoacetate, and 1,2-dibromoethane or α-halogenated carboxylic acid derivatives is presented.
References
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Journal ArticleDOI

Patterns in Hydrogen Bonding: Functionality and Graph Set Analysis in Crystals

TL;DR: In this article, a review of the most promising systematic approaches to resolving this enigma was initially developed by the late M. C. Etter, who applied graph theory to recognize, and then utilize, patterns of hydrogen bonding for the understanding and design of molecular crystals.
Journal ArticleDOI

An empirical correction for absorption anisotropy

TL;DR: A least-squares procedure is described for modeling an empirical transmission surface as sampled by multiple symmetry-equivalent and/or azimuth rotation-equ equivalent intensity measurements.
Related Papers (5)
Frequently Asked Questions (13)
Q1. What is the NH group formed with the imine N-atom?

The NH group forms an intramolecular hydrogen bond with the imine N-atom and thereby creates a six-membered loop with a graph set motif of S(6). 

The heterocyclic ring in molecule B also has an envelope conformation, but is more distorted from ideal geometry than the ring in molecule A and a different ring atom – C(25) – forms the envelope flap. 

The NH group in molecule A forms an intermolecular hydrogen bond with the imine N-atom of a neighboring mole-© 2005 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim www.eurjoc.org Eur. J. Org. Chem. 2005, 3128–31373130cule B. 

The formation of 1H-1,3,6-triazaaceanthrylene derivatives 5 occurred on heating of 1 and 4 in boiling pyridine without any additional reagents. 

The authors have recently shown that aryl isoselenocyanates 1 are convenient precursors for the introduction of selenium into five- and six-membered selenaheterocycles of types 3[50] and 5,[51] respectively (Scheme 1). 

The authors propose the following reaction mechanism for the formation of 9 and 10: addition of the primary amino group to 6 produces a selenourea derivative A, which undergoes a cyclization step to give the heterocyclic product. 

The heterocyclic ring in the major conformation has a slightly distorted half-chair conformation twisted on C(4a)–C(5a), with the distortion being in the direction of an envelope with C(5a) as the envelope flap. 

In the case of 9d, the methylene groups in the heterocyclic ring are disordered over two conformations, with the major conformation occurring in approximately 70% of the molecules. 

In the latter case, however, the product was obtained as the hydrochloride, which was very stable and gave the free amine derivative only with difficulty. 

Although syntheses of thiazines[27] and oxazines[28,29] are well known, those of the corresponding selenazines have been limited, owing to difficulties in the preparation of the selenium-containing starting materials. 

Chemical and spectroscopic evi-dence for the structures of all new compounds are presented,The chemistry of organoselenium compounds has attracted much attention, not only because of strong interest in these compounds as synthetic tools[1–8] but also as a result of their unique biological[9,10] and medicinal activities. 

The first equivalent of the base is needed to generate the free amine in situ, and the second to capture HX formed during the cyclization step. 

selenazoles have attracted attention in the chemistry of dye-stuffs,[41,42] as well as in medicine (antiinfective,[36] antiviral,[43] and antitumor agents[44]).