Efficient Synthesis of 2,3-Dihydro-1H-Perimidine Derivatives Using HBOB as a Novel Solid Acid Catalyst
Sunanda B. Phadtare A , R. Vijayraghavan B , Ganapati S. Shankarling A C and Douglas R. MacFarlane B CA Department of Dyestuff Technology, Institute of Chemical Technology, Matunga, Mumbai 400019, India.
B School of Chemistry, Monash University, Clayton Campus, Vic. 3800, Australia.
C Corresponding authors. Email: ganu23@gmail.com; douglas.macfarlane@monash.edu
Australian Journal of Chemistry 65(1) 86-90 https://doi.org/10.1071/CH11381
Submitted: 28 September 2011 Accepted: 17 October 2011 Published: 21 November 2011
Abstract
An efficient method for the synthesis of substituted 2,3-dihydro-1H-perimidine derivatives is described using bis(oxalato)boric acid (HBOB) as catalyst. The methodology provides an easily handled and recyclable catalyst for this type of reaction as an alternative platform to the conventional acid-catalyzed thermal processes. The time required to complete the reaction using HBOB was found to be shorter than conventional methods. Recycling of the catalyst has been efficiently achieved using a simple procedure.
References
[1] (a) K. Undheim, T. Benneche, in Comprehensive Heterocyclic Chemistry, 1996, 6, pp. 93–231 (Eds A. R. Katritzky, C. W. Rees, E. F. V. Scriven) (Pergamon: Oxford).(b) W. Wasulko, A. C. Noble, F. D. Popp, J. Med. Chem. 1966, 9, 599.
| Crossref | GoogleScholarGoogle Scholar |
[2] A. F. Pozharskii,, V. V. Dalnikovskaya, Russ. Chem. Rev. 1981, 50, 816.
[3] (a) J.-J. Vanden Eynde, D. Fromont, Bull. Soc. Chim. Belg. 1997, 106, 393.
| 1:CAS:528:DyaK1cXmtlQ%3D&md5=b263bc63393c11159fb078282c1f55a9CAS |
(b) J.-J. Vanden Eynde, F. Delfosse, T. V. Haverbeke, Tetrahedron 1995, 51, 5813.
| Crossref | GoogleScholarGoogle Scholar |
(c) J.-J. Vanden Eynde, F. Delfosse, A. Mayence, Y. V. Haverbeke, Tetrahedron 1995, 51, 5111.
(d) J.-J. Vanden Eynde, A. Mayence, A. Maquestiau, E. Anders, Heterocycles 1994, 37, 815.
| Crossref | GoogleScholarGoogle Scholar |
(e) J.-J. Vanden Eynde, A. Mayence, A. Maquestiau, E. Anders, Synth. Commun. 1992, 22, 3141.
| Crossref | GoogleScholarGoogle Scholar |
(f) A. Maquestiau, L. Berte, A. Mayence, J.-J. Vanden Eynde, Synth. Commun. 1999, 21, 2171.
| Crossref | GoogleScholarGoogle Scholar |
[4] R. Brehme, B. Stroede, J. Prakt. Chem. 1987, 329, 246.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaL1cXjslOqtg%3D%3D&md5=928594449d98e2d24d166820f6ec3978CAS |
[5] K. Honda, H. Nakanishi, A. Yabe, Bull. Chem. Soc. Jpn. 1983, 56, 2338.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaL2cXjsVGisA%3D%3D&md5=0763623176d0666b658459fec4128adaCAS |
[6] I. Yavari, M. Adib, F. Jahani-Moghaddam, H. B. Bijanzadeh, Tetrahedron 2002, 58, 6901.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD38XmsVWgsrw%3D&md5=94b8c47b5fb2152efb386447dda24031CAS |
[7] G. W. Rewcastle, in Comprehensive Heterocyclic Chemistry III: Perimidines and their Benzo Derivatives, 2008, 8, pp. 117–272 (Pergamon: Oxford, UK).
[8] (a) G. Sachs, Justus Liebigs Ann. Chem. 1909, 365, 162.
(b) U. T. Mueller-Westerhoff, B. Vance, D. I. Yoon, Tetrahedron 1991, 47, 909.
| Crossref | GoogleScholarGoogle Scholar |
(c) R. R. Reddy, C. V. C. Rao, Indian J. Heterocycl. Chem. 1993, 2, 199; S.-H. Kim, J. H. Kim, J. Z. Cui, Y. S. Gal, S. H. Jin, K. Koh, Dyes Pigm. 2002, 55, 1.
[9] (a) I. V. Aksenova, A. V. Aksenov, A. S. Lyakhovnenko, I. V. Borovlev, Chem. Heterocycl. Compd. 2008, 44, 891.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1cXhtlWhsLnP&md5=0d104edea0456f3ad29f84f643071be5CAS |
(b) J. Zhang, S. Zhang, Synth. Commun. 2007, 37, 2615.
| Crossref | GoogleScholarGoogle Scholar |
(c) Z. Yasaei, P. Mirzaei, A. Bazgir, C. R. Chim. 2010, 13, 1308.
| Crossref | GoogleScholarGoogle Scholar |
[10] M. M. Belmonte, E. C. Escudero-Adan, J. B. Buchholz, R. M. Haak, A. W. Kleij, Eur. J. Org. Chem. 2010, 4823.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3cXhtV2htb3L&md5=d4c95fb8a9ae0b55ed90e7bf76ea98f1CAS |
[11] J. Zhang, S. L. Zhang, J. M. Zhang, Chin. Chem. Lett. 2007, 18, 1057.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2sXht1KnsbvI&md5=54ccba2a3f794de00ffd5255946a581fCAS |
[12] S. L. Zhang, J. M. Zhang, Chin. J. Chem. 2008, 26, 185.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1cXitFagt7w%3D&md5=bdbd807220bdcebf8d2b17b8bbd83921CAS |
[13] W. Xu, C. A. Angell, Electrochem. Solid-State Lett. 2001, 4, E1.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3MXpvVWi&md5=db02afdfe129c8a3d49848eac2a4b544CAS |
[14] R. Vijayaraghavan, D. R. MacFarlane, Chem. Commun. 2004, 700.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2cXhvFOjsb0%3D&md5=ff3d223b9f7a5c4c627d512875c1744dCAS |
[15] R. Vijayaraghavan, R. D. R. MacFarlane, Macromolecules 2007, 40, 6515.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2sXovFCltbc%3D&md5=ee99f564c142f9c45fdfb894197bbf07CAS |
[16] F. Claude, Eur. Pat. FP 97–100109, 1997; U. Wietelmann, U. Lischka, K. Schade, J. C. Panitz, U.S. Pat. US 7,208,131 B2, 2007.