Tandem Esterification/1,4-Addition-Type Friedel–Crafts Alkylation Reactions of Phenols/Naphthols with Olefinic Thioazlactones: Access to Functionalized 1,2-Dihydrobenzo[f]chromen-3-ones and 3,4-Dihydrochromen-2-ones

作者: Azim Ziyaei Halimehjani , Maryam Khoshdoun

DOI: 10.1021/ACS.JOC.6B00740

关键词:

摘要: An efficient approach for the synthesis of novel alkyl 2,3-dihydro-3-oxo-1-aryl-1H-benzo[f]chromen-2-ylcarbamodithioates and 3,4-dihydro-2-oxo-4-aryl-2H-chromen-3-ylcarbamodithioates from 2-(alkylthio)thioazlactones (thioazlactones) phenols or naphthols catalyzed by PTSA was developed. The reaction proceeds via a domino esterification/intramolecular 1,4-addition-type Friedel–Crafts alkylation to afford interesting complex molecules simple procedure with high yields diastereoselectivity. X-ray analysis carried out firmly establish stereochemistry products.

参考文章(52)
DEBORAH M. ROLL, JOANN K. MANNING, GUY T. CARTER, Hongoquercins A and B, new sesquiterpenoid antibiotics: isolation, structure elucidation, and antibacterial activity. The Journal of Antibiotics. ,vol. 51, pp. 635- 639 ,(1998) , 10.7164/ANTIBIOTICS.51.635
E. E. Schweizer, Deborah Meeder-Nycz, 2H- and 4H-1-Benzopyrans Chemistry of Heterocyclic Compounds: A Series Of Monographs. pp. 11- 139 ,(2008) , 10.1002/9780470187012.CH2
Antreas Afantitis, Georgia Melagraki, Haralambos Sarimveis, Panayiotis A. Koutentis, John Markopoulos, Olga Igglessi-Markopoulou, A novel QSAR model for predicting induction of apoptosis by 4-aryl-4H-chromenes. Bioorganic & Medicinal Chemistry. ,vol. 14, pp. 6686- 6694 ,(2006) , 10.1016/J.BMC.2006.05.061
I. Arenal, M. Bernabé, O. Cuevas, E. Fernández Alvarez, Reaction of 5(4h)-thiazolones with diazomethane Tetrahedron. ,vol. 39, pp. 1387- 1393 ,(1983) , 10.1016/S0040-4020(01)91909-X
Asa D. Melhado, Giovanni W. Amarante, Z. Jane Wang, Marco Luparia, F. Dean Toste, Gold(I)-Catalyzed Diastereo- and Enantioselective 1,3-Dipolar Cycloaddition and Mannich Reactions of Azlactones Journal of the American Chemical Society. ,vol. 133, pp. 3517- 3527 ,(2011) , 10.1021/JA1095045
Sukbok Chang, Robert H. Grubbs, A Highly Efficient and Practical Synthesis of Chromene Derivatives Using Ring-Closing Olefin Metathesis. Journal of Organic Chemistry. ,vol. 63, pp. 864- 866 ,(1998) , 10.1021/JO9712198
José Barluenga, Mónica Trincado, Eduardo Rubio, José M. González, Intramolecular Arylation Reactions of Alkenes: A Flexible Approach to Chromans and Tetrahydroquinoline Derivatives Journal of the American Chemical Society. ,vol. 126, pp. 3416- 3417 ,(2004) , 10.1021/JA0397299
Barry M. Trost, Hong C. Shen, Li Dong, Jean-Philippe Surivet, Unusual Effects in the Pd-Catalyzed Asymmetric Allylic Alkylations: Synthesis of Chiral Chromans Journal of the American Chemical Society. ,vol. 125, pp. 9276- 9277 ,(2003) , 10.1021/JA036052G
Cinzia Conti, Luca Proietti Monaco, Nicoletta Desideri, Design, synthesis and in vitro evaluation of novel chroman-4-one, chroman, and 2H-chromene derivatives as human rhinovirus capsid-binding inhibitors. Bioorganic & Medicinal Chemistry. ,vol. 19, pp. 7357- 7364 ,(2011) , 10.1016/J.BMC.2011.10.060