Efficient one-pot reductive alkylations of malononitrile with aromatic aldehydes and one-pot synthesis of new 2-amino-3-cyano-4H-chromenes

A powerful new one-pot method has been developed for the reductive alkylation of malononitrile with aromatic aldehydes. This new procedure has vastly improved the yield and efficiency and increased the scope for the aromatic aldehydes. Incorporating water as the catalyst in ethanol for the condensat...

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Main Author:	Tayyari, Fariba
Other Authors:	Sammelson, Robert E.
Format:	Others
Published:	2011
Subjects:	Nitriles > Synthesis. Alkylation. Aldehydes. Benzopyrans > Synthesis.
Online Access:	http://cardinalscholar.bsu.edu/handle/handle/188442 http://liblink.bsu.edu/uhtbin/catkey/1399195

id	ndltd-BSU-oai-cardinalscholar.bsu.edu-handle-188442
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spelling	ndltd-BSU-oai-cardinalscholar.bsu.edu-handle-1884422014-08-07T03:32:55ZEfficient one-pot reductive alkylations of malononitrile with aromatic aldehydes and one-pot synthesis of new 2-amino-3-cyano-4H-chromenesEfficient one pot reductive alkylations of malononitrile with aromatic aldehydes and one pot synthesis of new 2-amino-3-cyano-4H-chromenesTayyari, FaribaNitriles -- Synthesis.Alkylation.Aldehydes.Benzopyrans -- Synthesis.A powerful new one-pot method has been developed for the reductive alkylation of malononitrile with aromatic aldehydes. This new procedure has vastly improved the yield and efficiency and increased the scope for the aromatic aldehydes. Incorporating water as the catalyst in ethanol for the condensation step allows stoichiometric amounts of malononitrile and aldehyde to be employed. After dilution and cooling the reduction step takes place quickly and efficiently with sodium borohydride to give monosubstituted malononitriles.The product from the reductive alkylation of malononitrile with 2-quinolinecarboxaldehyde quickly rearranges to a novel indolizine on silica gel or with heat, while alkylation of the monosubstituted derivative provides an unsymmetrically disubstituted malononitrile.We have also investigated this improved one-pot reductive alkylation using various 2-hydroxybenzaldehydes where intramolecular cyclization occurs following the condensation step and various 2-amino-3-cyano-4H-chromenes are formed.Department of ChemistrySammelson, Robert E.2011-06-03T19:41:42Z2011-06-03T19:41:42Z20082008iii, 128 leaves : ill. ; 28 cm.LD2489.Z78 2008 .T399http://cardinalscholar.bsu.edu/handle/handle/188442http://liblink.bsu.edu/uhtbin/catkey/1399195Virtual Press
collection	NDLTD
format	Others
sources	NDLTD
topic	Nitriles -- Synthesis. Alkylation. Aldehydes. Benzopyrans -- Synthesis.
spellingShingle	Nitriles -- Synthesis. Alkylation. Aldehydes. Benzopyrans -- Synthesis. Tayyari, Fariba Efficient one-pot reductive alkylations of malononitrile with aromatic aldehydes and one-pot synthesis of new 2-amino-3-cyano-4H-chromenes
description	A powerful new one-pot method has been developed for the reductive alkylation of malononitrile with aromatic aldehydes. This new procedure has vastly improved the yield and efficiency and increased the scope for the aromatic aldehydes. Incorporating water as the catalyst in ethanol for the condensation step allows stoichiometric amounts of malononitrile and aldehyde to be employed. After dilution and cooling the reduction step takes place quickly and efficiently with sodium borohydride to give monosubstituted malononitriles.The product from the reductive alkylation of malononitrile with 2-quinolinecarboxaldehyde quickly rearranges to a novel indolizine on silica gel or with heat, while alkylation of the monosubstituted derivative provides an unsymmetrically disubstituted malononitrile.We have also investigated this improved one-pot reductive alkylation using various 2-hydroxybenzaldehydes where intramolecular cyclization occurs following the condensation step and various 2-amino-3-cyano-4H-chromenes are formed. === Department of Chemistry
author2	Sammelson, Robert E.
author_facet	Sammelson, Robert E. Tayyari, Fariba
author	Tayyari, Fariba
author_sort	Tayyari, Fariba
title	Efficient one-pot reductive alkylations of malononitrile with aromatic aldehydes and one-pot synthesis of new 2-amino-3-cyano-4H-chromenes
title_short	Efficient one-pot reductive alkylations of malononitrile with aromatic aldehydes and one-pot synthesis of new 2-amino-3-cyano-4H-chromenes
title_full	Efficient one-pot reductive alkylations of malononitrile with aromatic aldehydes and one-pot synthesis of new 2-amino-3-cyano-4H-chromenes
title_fullStr	Efficient one-pot reductive alkylations of malononitrile with aromatic aldehydes and one-pot synthesis of new 2-amino-3-cyano-4H-chromenes
title_full_unstemmed	Efficient one-pot reductive alkylations of malononitrile with aromatic aldehydes and one-pot synthesis of new 2-amino-3-cyano-4H-chromenes
title_sort	efficient one-pot reductive alkylations of malononitrile with aromatic aldehydes and one-pot synthesis of new 2-amino-3-cyano-4h-chromenes
publishDate	2011
url	http://cardinalscholar.bsu.edu/handle/handle/188442 http://liblink.bsu.edu/uhtbin/catkey/1399195
work_keys_str_mv	AT tayyarifariba efficientonepotreductivealkylationsofmalononitrilewitharomaticaldehydesandonepotsynthesisofnew2amino3cyano4hchromenes
_version_	1716710201540739072

Efficient one-pot reductive alkylations of malononitrile with aromatic aldehydes and one-pot synthesis of new 2-amino-3-cyano-4H-chromenes

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