Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Synthesis 2015; 47(03): 377-386
DOI: 10.1055/s-0034-1378675
DOI: 10.1055/s-0034-1378675
paper
Efficient Synthesis of 1,3-Disubstituted 1,3-Dihydro-2H-imidazo[5,1-b]quinazolin-9-ones by an Intramolecular Mannich-Type Reaction
Further Information
Publication History
Received: 22 July 2014
Accepted after revision: 19 September 2014
Publication Date:
13 November 2014 (online)
Abstract
A general and efficient method has been developed for the synthesis of 1,3-disubstituted 1,3-dihydroimidazo[5,1-b]quinazolin-9-ones. The process involves an intramolecular Mannich-type reaction of a 2-aminomethylquinazolin-4-one derivative with an aldehyde, and gives diastereomeric mixtures of the minor cis- and major trans-cycloadducts.
Supporting Information
- for this article is available online at http://www.thieme-connect.com/products/ejournals/journal/ 10.1055/s-00000084.
- Supporting Information
-
References
- 1a Johne S. Prog. Chem. Org. Nat. Prod. 1984; 46: 159
- 1b Johne S In The Alkaloids: Chemistry and Pharmacology . Vol. 29. Brossi A. Academic Press; New York: 1986. Chap. 2, 99
- 1c Besson T, Chosson E. Comb. Chem. High Throughput Screening 2007; 10: 903
- 2 Horton DA, Bourne GT, Smythe ML. Chem. Rev. 2003; 103: 893
- 3 Examples include raltitrexed (marketed as Tomudex for treatment of colorectal cancer), ispinesib (Phase II for solid tumors), and tempostatin (Phase II for bladder cancer).
- 4 Jankowski F, Verones V, Flouquet N, Carato P, Berthelot P, Lebegue N. Tetrahedron 2010; 66: 128
- 5 Jen T, Dienel B, Bowman H, Petta J, Helt A, Love B. J. Med. Chem. 1972; 15: 727
- 6 Hardtmann GE, Koletar G, Pfister OR. J. Med. Chem. 1975; 18: 447
- 7 Venuti MC, Jones GH, Alvarez R, Bruno JJ. J. Med. Chem. 1987; 30: 303
- 8 Chern J.-W, Tao P.-L, Wang K.-C, Gutcait A, Liu S.-W, Yen M.-H, Chien S.-L, Rong J.-K. J. Med. Chem. 1998; 41: 3128
- 9 Hirth KP, Mann E, Shawyer LK, Ullrich A, Keri G, Szekely I, Bajor T, Haimichael J, Orfi L, Levitzki A, Gazit A, Tang PT, Lammers R. US 6331555, 2001
- 10 Varma RS, Bahadur S, Agnihotri AK. J. Chem. Eng. Data 1981; 26: 103
- 11 Udupi RH, Kushnoor A, Bhat AR. J. Indian Chem. Soc. 1999; 76: 461
- 12 Arend M, Westermann B, Risch N. Angew. Chem. Int. Ed. 1998; 37: 1044
- 13 Knight SD, Overman LE, Pairaudeau G. J. Am. Chem. Soc. 1995; 117: 5776
- 14 See the experimental section and the Supporting Information for details.