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-00032269.xml
Download PDF
CC BY ND NC 4.0 · SynOpen 2019; 03(01): 11-15
DOI: 10.1055/s-0037-1611667
DOI: 10.1055/s-0037-1611667
paper
Palladium-Catalysed Intramolecular C–N versus C–C Coupling: The Effect of 1,8-peri-Interaction in the Naphthalene System
The Science and Engineering Research Board of the Department of Science and Technology under the Government of India is gratefully acknowledged for an Early Career Research Award to S. M. (Sanction no. ECR/2017/000537).
Further Information
Publication History
Received: 22 December 2018
Accepted after revision: 02 January 2019
Publication Date:
31 January 2019 (online)
Abstract
Palladium-catalysed competitive intramolecular C–N and C–C coupling of 2-amino-2′-bromodiarylsulfones has been carried out based on 1,8-peri-interactions for the synthesis of phenothiazinedioxide and benzonaphthathiophenedioxide derivatives. A DFT study has been performed that provides support for the influence of the 1,8-peri-interaction.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1611667.
- Supporting Information
-
References
- 1a Balasubramaniyan V. Chem. Rev. 1966; 66: 567
- 1b Robert J.-B, Sherfinski JS, Marsh RE, Roberts JD. J. Org. Chem. 1974; 39: 1152
- 1c Banoglu E, Duffel MW. Chem. Res. Toxicol. 1999; 12: 278
- 1d Hoefelmeyer JD, Gabbaï FP. Organometallics 2002; 21: 982
- 1e Mallinson PR, Smith GT, Wilson CC, Grech E, Wozniak K. J. Am. Chem. Soc. 2003; 125: 4259
- 1f Kilian P, Knight FR, Woollins JD. Coord. Chem. Rev. 2011; 255: 1387
- 2a Mondal S, Debnath S. Synthesis 2014; 46: 368
- 2b Mondal S, Debnath S. Tetrahedron Lett. 2014; 55: 1577
- 2c Mondal S, Debnath S, Das B. Tetrahedron 2015; 71: 476
- 2d Mondal S, Debnath S, Pal S, Das A. Synthesis 2015; 47: 3423
- 2e Debnath S, Mondal S. J. Org. Chem. 2015; 80: 3940
- 2f Debnath S, Mondal S. Synthesis 2016; 48: 710
- 2g Debnath S, Malakar S, Mondal S. ChemistrySelect 2017; 2: 3147
- 2h Debnath S, Mondal S. Tetrahedron Lett. 2018; 59: 2260
- 3a Carbone A, Lucas CL, Moody CJ. J. Org. Chem. 2012; 77: 9179
- 3b Hunt CA, Mallorga PJ, Michelson SR, Schwam H, Sondey JM, Smith RL, Sugrue MF, Shepard KL. J. Med. Chem. 1994; 37: 240
- 3c Kim G, Yeom HR, Cho S, Seo JH, Kim JY, Yang C. Macromolecules 2012; 45: 1847
- 3d Prinz H, Chamasmani B, Vogel K, Böhm KJ, Aicher B, Gerlach M, Günther EG, Amon P, Ivanov I, Müller K. J. Med. Chem. 2011; 54: 4247
- 3e Encío I, Morré DJ, Villar R, Gil MJ, Martínez-Merino V. Br. J. Cancer 2005; 92: 690
- 3f Chandrasekera NS, Bailey MA, Files M, Alling T, Florio SK, Ollinger J, Odingo JO, Parish T. PeerJ 2 e612
- 3g Svoboda J, Štádler M, Jandera A, Panajotová V, Kuchař M. Collect. Czech. Chem. Commun. 2000; 65: 1082
- 4a Das B, Madhusudhan P, Venkataiah B. J. Chem. Res. Synop. 2000; 200
- 4b Kato J, Kakehata H, Maekawa Y, Yamashita T. Chem. Commun. 2006; 4498
- 4c Cecchetti V, Calderone V, Tabarrini O, Sabatini S, Filipponi E, Testai L, Spogli R, Martinotti E, Fravolini A. J. Med. Chem. 2003; 46: 3670
- 4d Sabatini S, Kaatz GW, Rossolini GM, Brandini D, Fravolini A. J. Med. Chem. 2008; 51: 4321
- 4e Calderone V, Spogli R, Martelli A, Manfroni G, Testai L, Sabatini S, Tabarrini O, Cecchetti V. J. Med. Chem. 2008; 51: 5085
- 4f Martelli A, Manfroni G, Sabbatini P, Barreca ML, Testai L, Novelli M, Sabatini S, Massari S, Tabarrini O, Masiello P, Calderone V, Cecchetti V. J. Med. Chem. 2013; 56: 4718
- 4g Li CS, Ding Y, Yang B.-J, Miklossy G, Yin H.-Q, Walker LA, Turkson J, Cao S. Org. Lett. 2015; 17: 3556
- 5 Debnath S, Mondal S. ChemistrySelect 2018; 3: 4129
- 6 The CCDC reference number for the CIF file of compound 8a is CCDC 1481104. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif
- 7 The CCDC reference number for the CIF file of compound 8f is CCDC 1481105. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif
- 8 Beletskaya IP, Cheprakov AV. Chem. Rev. 2000; 100: 3009
- 9 Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Scalmani G, Barone V, Mennucci B, Petersson GA, Nakatsuji H, Caricato M, Li X, Hratchian HP, Izmaylov AF, Bloino J, Zheng G, Sonnenberg JL, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Vreven T, Montgomery Jr JA., Peralta JE, Ogliaro F, Bearpark M, Heyd JJ, Brothers E, Kudin KN, Staroverov VN, Kobayashi R, Normand J, Raghavachari K, Rendell A, Burant JC, Iyengar SS, Tomasi J, Cossi M, Rega N, Millam JM, Klene M, Knox JE, Cross JB, Bakken V, Adamo C, Jaramillo J, Gomperts R, Stratmann RE, Yazyev O, Austin AJ, Cammi R, Pomelli C, Ochterski JW, Martin RL, Morokuma K, Zakrzewski VG, Voth GA, Salvador P, Dannenberg JJ, Dapprich S, Daniels AD, Farkas O, Foresman JB, Ortiz JV, Cioslowski J, Fox DJ. Gaussian 09. Gaussian Inc.; Wallingford, CT: 2009