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Synthesis of 2,8-diamino-5-hydroxy-4H,10H-pyrano[2,3-f]chromene-3,9-dicarbonitrile
Victor V. Dotsenko
* 1, 2, 3 ,
Ivan V. Didenko
1 ,
Gennady D. Krapivin
4 ,
Nikolay A. Aksenov
3 ,
Inna V. Aksenova
3 ,
Sergey G. Krivokolysko
2, 5
1  Kuban State University, 149 Stavropolskaya Str., Krasnodar 350040, Russian Federation
2  ChemEx Lab, Vladimir Dal’ Lugansk National University, Lugansk, 91034 Russia.
3  North-Caucasus Federal University, 1 Pushkina St., 355009 Stavropol, Russian Federation
4  Kuban State Technological University, 2 Moskovskaya st., 350072 Krasnodar, Russian Federation
5  Lugansk State Medical University, 1-g 50 years of Lugansk Defence, Lugansk 91045, Russia
Published: 03 November 2016 by MDPI in The 20th International Electronic Conference on Synthetic Organic Chemistry session General Organic Synthesis
https://doi.org/10.3390/ecsoc-20-a059
Abstract:

The reactions of phloroglucinol with α,β-unsaturated dinitriles (or malononitrile and carbonyl compounds) lead to the formation of hitherto unknown 2,8-diamino-5-hydroxy-4H,10H-pyrano[2,3-f]chromene-3,9-dicarbonitriles. The reaction conditions and the structure of the products were studied in details.

Keywords: phloroglucinol, malononitrile, isatin, NMR studies, X-ray studies, 2-amino-4H-pyran-3-carbonitrile, pyrano[2,3-f]chromene
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Comments on this paper
Mohamed Mahgoub
3 November 2016
Idea
Dear Sir,

What about if you take compound 3 with aldehyde and malononitrile 1:1:1 in the same condition to synthesis compound 4 ?

Regards,
M. Mahgoub
Victor Dotsenko
3 November 2016
Dear colleague, thanks for your comments. We have tried to do it. The compound 3 remains unchanged, and was isolated along with arylmethylene malononitrile formed. Perhaps it would be worth to try harsher conditions. Best regards, Victor Dotsenko

Mahmoud Al-Jibouri
4 November 2016
You should take in consideration the change of catalysis like acid or base to govern the type of product of chromone and percent of yield
Mahmoud Al-Jibouri
4 November 2016
However , the pyran ring is so sensitive to autocyclization if it contains keto and amino groups in the 1 and 4 posiitions


 
 
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