Facile one-pot synthesis of novel ortho-aminocarbonitriles and dicyanoanilines fused to heterocycles via pseudo four-component reactions

1-Methylpiperidin-4-one and its sulfur and oxygen analogues undergo individual facile pseudo four-component reactions with two folds of malononitrile and various aldehydes by using ultrasonic irradiation and deficient quantities of pyrrolidine. As a consequence, ortho-aminocarbonitrile products are...

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Bibliographic Details
Published in:Tetrahedron 2016-03, Vol.72 (13), p.1699-1705
Main Authors: Mojtahedi, Mohammad M., Pourabdi, Ladan, Abaee, M. Saeed, Jami, Hamed, Dini, Masoud, Halvagar, Mohammad R.
Format: Article
Language:English
Subjects:
Aldehydes
Dicyanoanilines
Formations
Irradiation
Malononitrile
ortho-Aminocarbonitriles
Oxygen
Piperidin-4-one
Pyran-4-one
Sonochemistry
Sulfur
Synthesis (chemistry)
Tetrahedrons
Thiopyran-4-one
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Summary:1-Methylpiperidin-4-one and its sulfur and oxygen analogues undergo individual facile pseudo four-component reactions with two folds of malononitrile and various aldehydes by using ultrasonic irradiation and deficient quantities of pyrrolidine. As a consequence, ortho-aminocarbonitrile products are formed efficiently in the mixture within 1–2 min of irradiation. Alternatively, the same mixtures of the reactants would lead to direct high-yield formation of dicyanoanilines, a group of products which are also attainable in a stepwise manner starting from the respective ortho-aminocarbonitriles. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2016.02.023