A Synthetic and Structural Study of Arylselenoamides and 2,4-Diaryl-1,3- Selenazoles

Abstract

The systematic preparation of 2,4-diaryl-1,3-selenazoles was carried out by two-component cyclization of the primary selenoamides with α-halo ketones. Selenoamides were obtained from the reaction of Woollins’ reagent with arylnitrile, followed by hydrolysis with water. Three selenoamides have close structural similarities along with intermolecular interactions such as the strong N–H···O hydrogen bonding, the weak N–H···Se, C–H···O/N/Se intermolecular interactions and π–π stacking interactions; meanwhile, the newly formed five-membered N–C–Se–C–C rings in ten 2,4-diaryl-1,3-selenazoles have either planar or near-planar conformations along with the weak C–H···O/N/Se/Br/Cl intermolecular interactions and π–π stacking interactions. In addition, the weak Se···Se close contacts in four cases and the C–H···N intramolecular interactions in two structures were also observed within the all solid structures.

Key words

selenoamides - 1,3-selenazoles - Woollins’ reagent - X-ray crystal structures - α-halo ketones

• References and Notes

• 1 Wirth T. Organoselenium Chemistry: Modern Development in Organic Synthesis. Springer; Berlin: 2000
• 2a Srivastava PC, Robin RK. J. Med. Chem. 1983; 26: 445
• 2b Kumar Y, Green R, Borysko KZ, Wise DS, Wotring L, Townsend LB. J. Med. Chem. 1993; 36: 3843
• 2c Koketsu M, Hishihara H, Wu W, Murakami K, Saiki I. Eur. J. Pharm. Sci. 1999; 9: 156
• 3a Garin J. Adv. Heterocycl. Chem. 1995; 62: 249
• 3b Uemoto T. Adv. Heterocycl. Chem. 1995; 64: 323
• 4a Organoselenium Chemistry. A Practical Approach. Back TG. Oxford University Press; Oxford: 1999
• 4b Mlochowski J. Phosphorus, Sulfur Silicon Relat. Elem. 1998; 191: 136
• 4c Tiecco M. Top. Curr. Chem. 2000; 208: 7
• 4d Wirth T. Angew. Chem. Int. Ed. 2000; 208: 3742
• 4e Mlochowski J, Brzaszcz M, Giurg M, Palus J, Wojtowicz H. Eur. J. Org. Chem. 2003; 4329
• 5 Shafiee A, Shafaati A, Habibi-Khamench B. J. Heterocycl. Chem. 1989; 26: 709
• 6 Wu W, Murakami K, Koketsu M, Yamada Y, Saiki I. Anticancer Res. 1999; 19: 5375
• 7 Cho SI, Koketsu M, Ishihara H, Matsushita M, Nairn AC, Fukazawa H, Uehara Y. Biochim. Biophys. Acta 2000; 1475: 207
• 8 Koketsu M, Choi SY, Ishihara H, Lim BO, Kim H, Kim SY. Chem. Pharm. Bull. 2002; 50: 1594
• 9 Gutzkow KB, Lahne HU, Naderi S, Torgersen KM, Skalhegg B, Koketsu M, Uehara Y, Blomhoff HK. Cell. Signalling 2003; 15: 871
• 10 Narender M, Reddy MS, Kumar VP, Reddy VP, Nageswar YV. D, Rao KR. J. Org. Chem. 2007; 72: 1849
• 11 Al-Rubaie AZ, Al-Masoudi WA, Hameed AJ, Yousif LZ, Graia M. J. Korean Chem. Soc. 2008; 52: 36
• 12a Klayman DL, Griffins TS. J. Am. Chem. Soc. 1973; 95: 197
• 12b Lai LL, Reid DH. Synthesis 1993; 870
• 13a Koketsu M, Fukuta Y, Nada F. J. Am. Chem. Soc. 2001; 123: 8408
• 13b Koketsu M, Fukuta Y, Ishihara H. Tetrahedron Lett. 2001; 42: 6333
• 14 Ogawa A, Miyaka J, Karasaki Y, Murai S, Sonoda N. J. Org. Chem. 1985; 50: 384
• 15a Geisler K, Jacobs A, Kunzler A, Mathes M, Girrleit H, Zimmermann B, Bulka E, Pferffer WD, Langer P. Synlett 2002; 1983
• 15b Geisler K, Pfeiffer WD, Künzler A, Below H, Bulka E, Langer P. Synthesis 2004; 875
• 16 Kamminski R, Glass RS, Skowronska A. Synthesis 2001; 1308
• 17 Cohen VJ. Synthesis 1978; 668
• 18 Shimada K, Hikage S, Takeishi Y, Takigawa Y. Chem. Lett. 1990; 1403
• 19 Ishihara H, Yosimuura K, Kouketsu M. Chem. Lett. 1998; 1287
• 20 Gray IP, Bhattacharyya P, Slawin AM. Z, Woollins JD. Chem. Eur. J. 2005; 11: 6221
• 21 Hua G, Woollins JD. Angew. Chem. Int. Ed. 2009; 48: 1368
• 22 Gomez CJ. A, Romano RM, Beckers H, Willner H, Della VC. O. Inorg. Chem. 2010; 49: 9972
• 23 Abdo M, Zhang Y, Schramm VL. Org. Lett. 2010; 12: 2982
• 24 Wong RC. S, Ooi ML. Inorg. Chim. Acta 2011; 366: 350
• 25 Hua G, Griffin JM, Ashbrook SE, Slawin AM. Z, Woollins JD. Angew. Chem. Int. Ed. 2011; 50: 4123
• 26 Hua G, Du J, Slawin AM. Z, Woollins JD. Inorg. Chem. 2013; 52: 8214
• 27 Hua G, Randall RA. M, Slawin Cordes DB, Crawford L, Bühl M, Woollins JD. Chem. Commun. 2013; 49: 2619
• 28 Hua G, Li Y, Slawin AM. Z, Woollins JD. Org. Lett. 2006; 8: 5251
• 29 Ogawa A, Miyaka J, Karasaki Y, Murai S, Sonoda N. J. Org. Chem. 1985; 50: 384
• 30 Al-Rubaie AZ, Yousif LL, Al-Hamad AJ. H. J. Organomet. Chem. 2002; 656: 274
• 31 Lai LL, Reid DH. Synthesis 1993; 870
• 32 Cohen VJ. Synthesis 1978; 668
• 33 Kuketsu Y, Takenaka H, Ishihara H. Heteroat. Chem. 2003; 14: 106
• 34 Aithen GB, Draga GP, Duncan JL. J. Chem. Soc., Dalton Trans. 1972; 2103
• 35 Longhi R, Draga RS. Inorg. Chem. 1965; 4: 11
• 36 X-ray crystal data for compounds 1f,h,i and 2b–g,m–p can be obtained free of charge via www.ccdc.cam.ac.uk/conts/ retrieving.html or from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; fax [phone]; e-mail: [e-mail].
• 37 Li Y, Hua G, Slawin AM. Z, Woollins JD. Molecules 2009; 14: 884
• 38 Baillargeon P, Lussier T, Dory YL. J. Crystallogr. 2014; Article ID 371629; DOI: 10.1155/2014/371629
• 39 Khan MH, Hameed S, Akhtara T, Masuda JD. Acta Crystallogr., Sect. E: Struct. Rep. Online 2009; 65: o1333
• 40 Wu DH. Acta Crystallogr., Sect. C: Cryst. Struct. Commun. 2013; 69: 1545
• 41 Cordes DB, Hua G, Slawin AM. Z, Woollins JD. Acta Crystallogr., Sect. C: Cryst. Struct. Commun. 2011; 67: o509
• 42 Pauling L. The Nature of the Chemical Bond. Cornell University Press; Ithaca (NY, USA): 1960
• 43 Werz DB, Gleiter R, Rominger F. J. Org. Chem. 2002; 67: 4290
• 44 Hua G, Li Y, Fuller AL, Slawin AM. Z, Woollins JD. Eur. J. Org. Chem. 2009; 1612
• 45 Hua G, Cordes DB, Li Y, Slawin AM. Z, Woollins JD. Tetrahedron Lett. 2011; 52: 3311
• 46 Hua G, Henry JB, Li Y, Mount AR, Slawin AM. Z, Woollins JD. Org. Biomol. Chem. 2010; 8: 1655
• 47 Onyamboko NV, Renson M, Chapelle S, Granger P. Org. Magn. Reson. 1982; 19: 74
• 48 Beswick MA, Harmer CN, Raithby PR, Steiner A, Tombul M, Wright DS. J. Organomet. Chem. 1999; 573: 267
• 49 Hope H, Knobler C, McCullough JD. Acta Crystallogr., Sect. B: Struct. Crystallogr. Cryst. Chem. 1970; 26: 628
• 50 Li GM, Zingaro RA, Sergi M, Reibenspies JH, Nakajima T. Organometallics 1997; 16: 756
• 51 Koketsu M, Sakai T, Kiyokuni T, Garud DR, Ando H, Ishihara H. Heterocycles 2006; 68: 1607
• 52a Zhou YH, Linden A, Heimgartner H. Helv. Chim. Acta 2000; 83: 1576
• 52b Koketsu M, Nada F, Ishihara H. Synthesis 2002; 195