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

• Published in: Tetrahedron Vol. 72; no. 13; pp. 1699 - 1705
• Main Authors: Mojtahedi, Mohammad M., Pourabdi, Ladan, Abaee, M. Saeed, Jami, Hamed, Dini, Masoud, Halvagar, Mohammad R.
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 31.03.2016; Elsevier
• Subjects: Aldehydes; Chemistry; Chemistry, Organic; Dicyanoanilines; Formations; Irradiation; Malononitrile; ortho-Aminocarbonitriles; Oxygen; Physical Sciences; Piperidin-4-one; Pyran-4-one; Science & Technology; Sonochemistry; Sulfur; Synthesis (chemistry); Tetrahedrons; Thiopyran-4-one; VLGSDIRAROUSRY-UHFFFAOYSA-N; LWTFWYYRILFLSM-UHFFFAOYSA-N; Piperidin-4-one; GLTPZAGLCSGAKP-UHFFFAOYSA-N; CCKWFVSTTBMJRJ-UHFFFAOYSA-N; HIYHMXMNHKZUJR-UHFFFAOYSA-N; WGMBQYIBNHRLRP-UHFFFAOYSA-N; DEUBHKWGJASWCS-UHFFFAOYSA-N; ZCLBAIXFQUCONY-UHFFFAOYSA-N; Dicyanoanilines; JNUYOQQSJNOBBN-UHFFFAOYSA-N; RXTFAAXINIBMQQ-UHFFFAOYSA-N; YAZKGJGFMCZVPV-UHFFFAOYSA-N; Sonochemistry; KUIJMWMPSTWTII-UHFFFAOYSA-N; MHEXGVRAEIUOPJ-UHFFFAOYSA-N; WPEOSHQNWZGDCB-UHFFFAOYSA-N; Thiopyran-4-one; OCUCXWLHEUOTIN-UHFFFAOYSA-N; Pyran-4-one; OMEVRFWLDALZEV-UHFFFAOYSA-N; WYXFBCOURCVFIB-UHFFFAOYSA-N; RVDFIOJUTBIDKB-UHFFFAOYSA-N; SARRDIJZAAJKHI-UHFFFAOYSA-N; ortho-Aminocarbonitriles; ILHARBNPOBLAPB-UHFFFAOYSA-N; ROUTE; ACID; EFFICIENT SYNTHESIS; CARBONYL-COMPOUNDS; CARBOCYCLES; MULTICOMPONENT REACTIONS; 2,6-DICYANOANILINES; MALONONITRILE; SYSTEMS; MONOARYLIDENE DERIVATIVES
• ISSN: 0040-4020; 1464-5416
• DOI: 10.1016/j.tet.2016.02.023

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]