Morpholine Catalyzed One‐pot Multicomponent Synthesis of Compounds Containing Chromene Core in Water

A series of dihydropyrano[c]chromene was obtained via condensation of aldehyde, malononitrile and 4-hydroxycoumarin in water catalyzed by morpholine, as a one-pot reaction. The significance of our findings relates to reducing the use of organic solvents, potentially toxic and hazardous materials, as well as its simplicity, good yields, mild conditions, and lower costs.

[1]  D. Shi,et al.  Synthesis of 2-Amino-4-Aryl-5-Oxo-4,5-Dihydropyrano[3,2-c] Chromene Derivatives Catalysed by KF-Montmorillonite , 2008 .

[2]  S. Balalaie,et al.  Novel and efficient catalysts for the one-pot synthesis of 3,4-dihydropyrano[c]chromene derivatives in aqueous media , 2007 .

[3]  Liang Chen,et al.  Organic chemistry in water. , 2006, Chemical Society reviews.

[4]  K. Jørgensen,et al.  Organocatalytic enantioselective nucleophilic vinylic substitution. , 2006, Angewandte Chemie.

[5]  M. Kidwai,et al.  Convenient Preparation of Pyrano Benzopyranes in Aqueous Media , 2006 .

[6]  Y. Wan,et al.  Sequential Aldol/Michael Addition Reaction in Ionic Liquid Catalyzed by Morpholine: A Convenient Synthesis of 1,3,5‐Triaryl‐1,5‐pentanedione , 2006 .

[7]  Baomin Wang,et al.  Enantioselective nitroaldol reaction of alpha-ketoesters catalyzed by cinchona alkaloids. , 2006, Journal of the American Chemical Society.

[8]  S. Chandrasekhar,et al.  l-Proline catalysed asymmetric aldol reactions in PEG-400 as recyclable medium and transfer aldol reactions , 2006 .

[9]  T. Choshi,et al.  A new synthesis of 6-substituted pyrido[2,3-d]pyrimidines , 2002 .

[10]  R. Troschütz,et al.  Synthesis of 5-Substituted Pyrido[2,3-d]Pyrimidines as Analogues of the Antifolates Methotrexate, Ddathf and Pemetrexed(LY231514) , 2001 .

[11]  E. Stoyanov,et al.  General Method for the Preparation of Substituted 2-Amino-4H,5H-pyrano(4,3-b)pyran-5-ones and 2-Amino-4H-pyrano(3,2-c)pyridine-5-ones , 2000 .

[12]  A. Bedair,et al.  Heteroaromatization with 4-Hydroxycoumarin Part I: Synthesis of some new Pyranocoumarins and Coumarinopyranopyrimidines † , 2000 .

[13]  V. Ram,et al.  An Elegant Approach Towards the Regioselective Synthesis of Deazalumazines Through Nucleophile Induced Ring Transformation Reactions of 6-Aryl-3-cyano-4-methylthio-2H-pyran-2-ones , 2000 .

[14]  M. R. Mahran,et al.  Reactions of 4-Hydroxycoumarin and 4-Hydroxyfurocoumarins with α,β-Unsaturated Nitriles. Mass Spectrometry of the New γ-Pyrano-α-pyran Derivatives , 1999 .

[15]  Rajender S. Varma,et al.  Solvent-free organic syntheses. using supported reagents and microwave irradiation , 1999 .

[16]  E. Taylor,et al.  Synthesis of a Pyrido[2,3-d]pyrimidine Analogue of the Multitargeted Antifolate LY231514 , 1997 .

[17]  A. Calignano,et al.  Synthesis and pharmacological activity of 2-oxo-(2H) 1-benzopyran-3-carboxamide derivatives , 1993 .

[18]  Rakesh Kumar,et al.  A convenient synthesis of 1,3-diaryl-1,2,3,4,-tetrahydro-5,7,7-trimethyl-4-oxo-2-thioxo-7H-pyrano[ 2 ,3-d ]pyrimidines , 1990 .

[19]  G. Anderson,et al.  Pyrido(2,3-d)pyrimidines. IV. Synthetic studies leading to various oxopyrido(2,3-d)pyrimidines. , 1976, The Journal of organic chemistry.

[20]  A. D. Broom,et al.  Pyrido(2,3-d)pyrimidines. 3. Synthesis of some 8-( -D-ribofuranosyl)pyrido(2,3-d)pyrimidines structurally related to the antibiotic sangivamycin. , 1972, The Journal of organic chemistry.

[21]  A. D. Broom,et al.  Studies on the acylation of some 6-aminouracil derivatives. , 1972, The Journal of organic chemistry.

[22]  K. P. Link,et al.  Studies on the 4-Hydroxycoumarins. XVIII.1a 3-[α-(Acetamidomethyl)benzyl]-4-hydroxycoumarin and Related Products1b , 1962 .