Large scale Biginelli reaction via water-based biphasic media: A green chemistry strategy

Tetrahedron Letters

Volumn 46, Issue 11, 2005, Pages 1901-1903

  Bose, Ajay K ^a   Manhas, Maghar S ^a   Pednekar, Suhas ^a   Ganguly, Subhendu N ^a   Dang, Hoang ^a   He, William ^a   Mandadi, Arun ^a  

^a Stevens Institute of Technology   (United States)

Author keywords

Biginelli reaction; Biphasic media; Dihydropyrimidinones; p TSA as catalyst

Indexed keywords

SULFONIC ACID DERIVATIVE; WATER;

ARTICLE; BIGINELLI REACTION; CATALYSIS; CHEMICAL REACTION KINETICS; CHEMISTRY; ENERGY CONSUMPTION; GREEN CHEMISTRY;

EID: 14044276235     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.01.087     Document Type: Article

References (11)

1. P. Biginelli Gazz. Chim. Ital. 23 1893 360
2. For extensive citations of diverse types of physiological activities, see literature cited in Ref. 4
3. Previously reported reactions were conducted on a few hundred milligram scale
4. K.V.N.S. Srinivas, and B. Das Synthesis 2004 2091
5. Q. Sun, Y.-q. Wang, Z.-m. Ge, T.-m. Cheng, and R.-t. Li Synthesis 2004 1047
6. S. Tu, F. Fang, S. Zhu, T. Li, X. Zhang, and Q. Zhuang Synlett 2004 537
7. For extensive citation of earlier literature, see Ref. 4
8. O. Kappe, D. Kumar, and R.S. Varma Synthesis 1999 1799
9. A.K. Bose, S. Pednekar, S.N. Ganguly, G. Chakraborty, and M.S. Manhas Tetrahedron Lett. 45 2004 8351
10. (a) Typical experimental procedure for the Biginelli reaction: An aromatic aldehyde (1 mol) was added to 150 mL of water with vigorous stirring. Then to this mixture was added urea/thiourea (2 mol) followed by the addition of ethylacetoacetate (1 mol), with constant stirring. Finally 5 g of p-toluenesulfonic acid was added to the above reaction mixture. During stirring a white crystalline solid separated out. After 15 min of stirring, this solid was filtered, washed with water and dried. It was recrystallized from methanol/ethyl acetate. The yields and melting points of the products are reported in Table 1. (b) Typical experimental procedure for N-acetylation: An aromatic amine (1 mol) was added to 110 mL of water with vigorous stirring. Then to it was added 102 mL (1 mol) of acetic anhydride. During stirring a white crystalline solid separted out. After 15 min of stirring the reaction mixture was allowed to cool and filtered. The solid product was washed with ice cold water and dried
11. This is Green Chemistry Part 2. For the previous paper, see: A.K. Bose, S. Pednekar, S.N. Ganguly, G. Chakraborty, and M.S. Manhas Tetrahedron Lett. 45 2004 8351