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 2017; 49(03): 693-703
DOI: 10.1055/s-0036-1588071
DOI: 10.1055/s-0036-1588071
paper
A Domino Aza-Prins/Friedel–Crafts Reaction for the Synthesis of Benzomorphans
Further Information
Publication History
Received: 11 August 2016
Accepted: 18 August 2016
Publication Date:
14 September 2016 (online)
Abstract
A new domino sequence involving an aza-Prins cyclization and a Friedel–Crafts reaction is reported. The starting materials are N-tosylimines prepared in situ from N-tosylated homoallylamines and derivatives of phenylacetaldehyde. The domino reactions are mediated by Brønsted and Lewis acids and give benzoannelated azabicyclononanes. Many derivatives thereof contain the benzomorphan scaffold and are thus of pharmaceutical interest as analgesics. The method provides a one-step access to substituted benzomorphans from readily available starting materials. The yields are generally good and various substituents are tolerated.
Key words
arylation - cyclization - imines - aza-Prins reaction - Friedel–Crafts reaction - morphine - pentazocine - domino reactionSupporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0036-1588071.
- Supporting Information
-
References
- 1 Blakemore PR, White JD. Chem. Commun. 2002; 1159
- 2 Li Y, Feng C, Shi H, Xu X. Org. Lett. 2016; 18: 324
- 3a Albertson NF, Wetterau WF. J. Med. Chem. 1970; 13: 302
- 3b Anada M, Tanaka M, Washio T, Yamawaki M, Abe T, Hashimoto S. Org. Lett. 2007; 9: 4559
- 3c Archer S, Albertson NF, Harris LS, Pierson AK, Bird JG. J. Med. Chem. 1964; 7: 123
- 3d Chen Q, Huo X, Yang Z, She X. Chem. Asian J. 2012; 7: 2543
- 3e Coe JW, Brooks PR, Vetelino MG, Bashore CG, Bianco K, Flick AC. Tetrahedron Lett. 2011; 52: 953
- 3f Comins DL, Zhang Y.-m, Joseph SP. Org. Lett. 1999; 1: 657
- 3g Genisson Y, Marazano C, Das BC. J. Org. Chem. 1993; 58: 2052
- 3h Kametani T, Huang S.-P, Ihara M, Fukumoto K. J. Org. Chem. 1976; 41: 2545
- 3i Kametani T, Kigasawa K, Hayasaka M, Wakisaka K, Satoh F, Aoyama T, Ishimaru H. J. Heterocycl. Chem. 1971; 8: 769
- 3j Kametani T, Kigasawa K, Hüragi M, Hayasaka T, Wagatsuma N, Wakisaka K. J. Heterocycl. Chem. 1969; 6: 43
- 3k Meyers AI, Dickman DA, Bailey TR. J. Am. Chem. Soc. 1985; 107: 7974
- 3l Palmer DC, Strauss MJ. Chem. Rev. 1977; 77: 1
- 3m Trost BM, Tang W. J. Am. Chem. Soc. 2003; 125: 8744
- 3n Yang X, Zhai H, Li Z. Org. Lett. 2008; 10: 2457
- 5 Olier C, Kaafarani M, Gastaldi S, Bertrand MP. Tetrahedron 2010; 66: 413
- 6a Hanschke E. Chem. Ber. 1955; 88: 1053
- 6b Jasti R, Vitale J, Rychnovsky SD. J. Am. Chem. Soc. 2004; 126: 9904
- 6c Tsui GC, Liu L, List B. Angew. Chem. Int. Ed. 2015; 54: 7703
- 7 Crane EA, Scheidt KA. Angew. Chem. Int. Ed. 2010; 49: 8316
- 8a Han X, Peh G, Floreancig PE. Eur. J. Org. Chem. 2013; 1193
- 8b Hinkle RJ, Lewis SE. Org. Lett. 2013; 15: 4070
- 8c Reddy BV. S, Borkar P, Yadav JS, Sridhar B, Grée R. J. Org. Chem. 2011; 76: 7677
- 8d Reddy BV. S, Reddy MR, Reddy SG, Sridhar B, Kumar SK. Eur. J. Org. Chem. 2015; 3103
- 8e Subba Reddy BV, Borkar P, Yadav JS, Purushotham Reddy P, Kunwar AC, Sridhar B, Grée R. Org. Biomol. Chem. 2012; 10: 1349
- 8f Subba Reddy BV, Kumar H, Borkar P, Yadav JS, Sridhar B. Eur. J. Org. Chem. 2013; 1993
- 8g Subba Reddy BV, Medaboina D, Sridhar B. J. Org. Chem. 2014; 80: 653
- 8h Subba Reddy BV, Medaboina D, Sridhar B, Singarapu KK. J. Org. Chem. 2013; 78: 8161
- 8i Subba Reddy BV, Medaboina D, Sridhar B, Singarapu KK. J. Org. Chem. 2014; 79: 2289
- 8j Subba Reddy BV, Prudhvi Raju N, Someswarao B, Mohan Reddy BJ, Sridhar B, Marumudi K, Kunwar AC. Org. Biomol. Chem. 2015; 13: 4733
- 8k Subba Reddy BV, Swathi V, Swain M, Bhadra MP, Sridhar B, Satyanarayana D, Jagadeesh B. Org. Lett. 2014; 16: 6267
- 8l Subba Reddy BV, Venkateswarlu A, Sridevi B, Marumudi K, Kunwar AC, Gayatri G. Org. Biomol. Chem. 2015; 13: 2669
- 9a Reddy UC, Bondalapati S, Saikia AK. J. Org. Chem. 2009; 74: 2605
- 9b Tian X, Jaber JJ, Rychnovsky SD. J. Org. Chem. 2006; 71: 3176
- 10 Subba Reddy BV, Medaboina D, Sridhar B. J. Org. Chem. 2015; 80: 653
- 11 Weidmann V, Ploog J, Kliewer S, Schaffrath M, Maison W. J. Org. Chem. 2014; 79: 10123
- 12a Mekhalfia A, Markó IE. Tetrahedron Lett. 1991; 32: 4779
- 12b Mekhalfia A, Markó IE, Adams H. Tetrahedron Lett. 1991; 32: 4783
- 13a Parchinsky V, Shumsky A, Krasavin M. Tetrahedron Lett. 2011; 52: 7157
- 13b Parchinsky V, Shumsky A, Krasavin M. Tetrahedron Lett. 2011; 52: 7161
- 13c Durel V, Lalli C, Roisnel T, Weghe P. J. Org. Chem. 2016; 81: 849
- 14a Miranda PO, Carballo RM, Martín VS, Padrón JI. Org. Lett. 2009; 11: 357
- 14b Speckamp WN, Moolenaar MJ. Tetrahedron 2000; 56: 3817
- 14c Royer J, Bonin M, Micouin L. Chem. Rev. 2004; 104: 2311
- 15a Silva LF. Jr, Quintiliano SA. Tetrahedron Lett. 2009; 50: 2256
- 15b Dobbs AP, Guesné SJ. J, Martinović S, Coles SJ, Hursthouse MB. J. Org. Chem. 2003; 68: 7880
- 15c Dobbs AP, Guesne SJ. J, Parker RJ, Skidmore J, Stephenson RA, Hursthouse MB. Org. Biomol. Chem. 2010; 8: 1064
- 16 Oshita M, Okazaki T, Ohe K, Chatani N. Org. Lett. 2005; 7: 331
- 17 Verendel JJ, Zhou T, Li J.-Q, Paptchikhine A, Lebedev O, Andersson PG. J. Am. Chem. Soc. 2010; 132: 8880
- 18a Miao L, Haque I, Manzoni MR, Tham WS, Chemler SR. Org. Lett. 2010; 12: 4739
- 18b Lin CH, Haadsma-Svensson SR, Phillips G, Lahti RA, McCall RB, Piercey MF, Schreur PJ. K. D, Von Voigtlander PF, Smith MW, Chidester CG. J. Med. Chem. 1993; 36: 1069
- 18c Chidester CG, Lin CH, Lahti RA, Haadsma-Svensson SR, Smith MW. J. Med. Chem. 1993; 36: 1301
- 19 Kresze G, Wagner U. Liebigs Ann. Chem. 1972; 762: 93
- 20 Leger PR, Murphy RA, Pushkarskaya E, Sarpong R. Chem. Eur. J. 2015; 21: 4377