Synthesis of 2-amide-3-carboxylate-4-aryl-
Received: 3 January 2012 / Accepted: 20 January 2012 / Published online: 3 February 2012
Ó Springer Science+Business Media B.V. 2012
Tetrabutyl ammonium bromide (TBAB) catalyzed one-pot synthesis of
4H-chromene via a three-component cyclocondensation of aryl aldehydes, cyanoacetate
and dimedone in green media–water. Then, 4H-chromene reacted with acyl chloride in
acetonitrile at reﬂuxing with catalytic amount of DMAP to yield the title compounds in
good yields. The structures of all title compounds were conﬁrmed by
H NMR, MS and
elementary analyses. The X-ray crystallography of compound 3n indicated that there
were strong intermolecular hydrogen bonds.
Keywords Aromatic aldehydes Á Cyanoacetate Á Dimedone Á One-pot synthesis Á
4H-chromene Á 2-amide-3-carboxylate-4H-chromene
Heterocyclic compounds, especially pyran and benzopyran derivatives, have played
an important role in medicines, pesticides, dyes, and other ﬁne chemical industries.
Pyran ring, because of its intrinsic activity, has become a very useful synthon for
other heterocyclic compounds . Benzopyran derivatives exhibit excellent
physiological and pharmacological activity , such as anti-hypoplasia , anti-
allergic effects , treatment of allergic bronchitis , and anti-cancer .
Furthermore, amides occupy an important place in medicines and pesticides due
to their broad-spectrum, high-efﬁciency active features, for example, bactericidal
, acaricidal , pesticidal , herbicidal , and other biological activities.
In order to ﬁnd bioactive compounds, we designed and synthesized a series of
Z. Zeng Á L. Wang Á Y. Cao Á Y. Luo (&)
Key Laboratory of Protection and Development Utilization of Tropical Crop Germplasm Resources,
Ministry of Education, College of Environment and Plant Protection, Hainan University, Haikou,
Hainan 570228, People’s Republic of China
Res Chem Intermed (2012) 38:1751–1760