Synlett
DOI: 10.1055/s-0036-1590980
letter
© Georg Thieme Verlag Stuttgart · New York

An Approach to the Diastereoselective Synthesis of Cyclohexane-1,3-dicarboxamide Derivatives via a Pseudo Five-Component ­Reaction Based on Diketene

Bahareh Talaei, Majid M. Heravi*, Hossein A. Oskooie, Atieh Rezvanian
Further Information

Publication History

Received: 01 July 2017

Accepted after revision: 06 September 2017

Publication Date:
19 September 2017 (eFirst)

Abstract

A one-pot pseudo five-component reaction for the synthesis of 2-aryl-4-hydroxy-4-methyl-6-oxo-N 1,N 3-dialkylcyclohexane-1,3-dicarboxamide derivatives involving different primary amines, various aromatic aldehydes, and diketene in the presence of triethylamine with high yields is achieved.

Supporting Information

 
  • References and Notes

    • 1a Mohamed SF. Youssef MM. Amr AE. Kotb ER. Sci. Pharm. 2008; 76: 279
    • 1b Martin DF. Shamma M. Fernelius WC. J. Am. Chem. Soc. 1958; 80: 5851
  • 2 Li Z. Liu J. Xia C. Li F. ACS Catal. 2013; 3: 2440
    • 3a Holland KD. Naritoku DK. McKeon AC. Ferrendelli JA. Covey DF. Mol. Pharmacol. 1990; 37: 98
    • 3b Kohli RP. Kishor K. Dua PR. Saxena RC. Indian J. Med. Res. 1967; 55: 1221
  • 4 Salem MA. I. Soliman EA. Smith MB. Mahmoud MR. Azab ME. Phosphorus, Sulfur Silicon Relat. Elem. 2004; 179: 61
  • 5 Fu Y. Ye F. Chem. Res. Chin. Univ. 2004; 20: 124
  • 6 Field J. Costa F. Boryczka A. Antibiot. Annu. 1958; 6: 547
    • 7a Shen C. Wu X.-F. Chem. Eur. J. 2017; 23: 2973
    • 7b Yan LJ. Wang YC. ChemistrySelect 2016; 1: 6948
    • 7c Garbarino S. Ravelli D. Protti S. Basso A. Angew. Chem. Int. Ed. 2016; 55: 15476
    • 7d Moni L. Banfi L. Riva R. Basso A. Synthesis 2016; 48: 4050
    • 8a Moradi WA. Decker M. Karig G. Himmler T. Lui N. Straub A. US 20100217018, 2010
    • 8b Li J.-H. Zhu Q.-M. Liang Y. Yang D. J. Org. Chem. 2005; 70: 5347
    • 8c Kaplaneris N. Koutoulogenis G. Raftopoulou M. Kokotos CG. J. Org. Chem. 2015; 80: 5464
    • 8d Jordan-Hore JA. Sanderson JN. Lee A.-L. Org. Lett. 2012; 14: 2508
    • 9a Sharma A. Pandey J. Tripathi R. Tetrahedron Lett. 2009; 50: 1812
    • 9b Gein VL. Nosova NV. Potemkin KD. Aliev ZG. Kriven’ko AP. Russ. J. Org. Chem. 2005; 41: 1016
    • 9c Gein V. Odegova T. Yankin A. Nosova N. Russ. J. Gen. Chem. 2015; 85: 46
    • 9d Dyachenko V. Karpov E. Russ. J. Org. Chem. 2014; 50: 1787
    • 9e Sargsyan M. Hayotsyan S. Khachatryan AK. Badasyan A. Panosyan G. Kon’kova S. Chem. Heterocycl. Compd. 2013; 48: 1805
  • 10 Srinivasan M. Perumal S. Tetrahedron 2006; 62: 7726
  • 11 Gein V. Levandovskaya E. Nosova N. Vakhrin M. Kriven’ko A. Aliev Z. Russ. J. Org. Chem. 2007; 43: 1096
  • 12 Gein V. Vagapov A. Nosova N. Voronina E. Vakhrin M. Kriven’ko A. Pharm. Chem. J. 2010; 44: 245
  • 13 Nitta H. Takimoto K. Chem. Pharm. Bull. 1992; 40: 858
  • 14 Geirsson JK. Arnadottir L. Jonsson S. Tetrahedron 2004; 60: 9149
    • 15a Sai KK. S. Gilbert TM. Klumpp DA. J. Org. Chem. 2007; 72: 9761
    • 15b Alizadeh A. Rezvanian A. Zhu LG. Tetrahedron 2008; 64: 351
    • 15c Alizadeh A. Rezvanian A. Bijanzadeh HR. Synthesis 2008; 725
  • 16 Clemens RJ. Chem. Rev. 1986; 86: 241
    • 17a Heravi MM. Talaei B. Adv. Heterocycl. Chem. 2016; 122: 1
    • 17b Heravi MM. Talaei B. Adv. Heterocycl. Chem. 2017; 125: in press
    • 18a Saeedi M. Heravi MM. Beheshtiha YS. Oskooie HA. Tetrahedron 2010; 66: 5345
    • 18b Heravi MM. Mousavizadeh F. Ghobadi N. Tajbakhsh M. Tetrahedron Lett. 2014; 55: 1226
    • 18c Mirsafaei R. Heravi MM. Ahmadi S. Moslemin MH. Hosseinnejad T. J. Mol. Catal. A: Chem. 2015; 402: 100
    • 18d Mirsafaei R. Heravi MM. Hosseinnejad T. Ahmadi S. Appl. Organomet. Chem. 2016; 30: 823
    • 18e Sadjadi S. Heravi MM. Nazari N. RSC Adv. 2016; 6: 53203
    • 18f Heravi M. Moghimi S. J. Iran. Chem. Soc. 2011; 8: 306
    • 18g Heravi MM. Baghernejad B. Oskooie HA. Hekmatshoar R. Tetrahedron Lett. 2008; 49: 6101
    • 18h Rezvanian A. Tetrahedron 2016; 72: 6428
    • 18i Rezvanian A. Tetrahedron 2015; 71: 4752
    • 19a Heravi MM. Daraie M. Molecules 2016; 21: 441
    • 19b Rezvanian A. Heravi MM. Shaabani Z. Tajbakhsh M. Tetrahedron 2017; 73: 2009
  • 20 Bhaska Kumar T. Dhananjaya G. Sumanth C. Vaishaly S. Botre G. Rao MS. Sekhar KB. C. Kumar KS. Pal M. RSC Adv. 2013; 3: 2207
  • 21 Typical Synthesis Procedure for 3a A solution of benzylamine (0.107 g, 1.0 mmol) and DK (0.084 g, 1.0 mmol) was magnetically stirred in dry CH2Cl2 (5 mL) for 2 h. Then, 4-chlorobenzaldehyde (0.106 g, 1.0 mmol) and triethylamine were added simultaneously. The reaction mixture was allowed to stir for 8 d at room temperature until a precipitate appeared. After completion of the reaction, as indicated by TLC (EtOAc/n-hexane, 1:2), the precipitate was filtered off, washed with diethyl ether, and dried in vacuum to give 3a. N 1,N 3-Dibenzyl-2-(4-chlorophenyl)-4-hydroxy-4-methyl-6-oxocyclohexane-1,3-dicarboxamide (3a) White powder (0.45 g, 90%); mp 262 °C. IR (KBr): 3743, 3301, 3093, 2924, 1721, 1644, 1551, 1498, 1455, 1424 (cm–1). 1H NMR (400 MHz, DMSO-d 6): δ = 1.22 (3 H, s, CH3), 2.38 (1 H, d, J = 14 Hz, CH), 2.74 (1 H, d, J = 14 Hz, CH), 3.11 (1 H, d, J = 12 Hz, CH), 3.71 (1 H, d, J = 12.4 Hz, CH), 3.87–3.92 (2 H, m, CH2), 3.94–4.00 (1 H, t, J = 9.3 Hz, CH), 4.31–4.37 (2 H, m, CH2), 4.96 (1 H, s, OH), 6.60–6.63 (4 H, m, H-Ar), 7.12–7.17 (6 H, m, H-Ar), 7.29 (2 H, d, J = 8.4 Hz, H-Ar), 7.36 (2 H, d, J = 8.4 Hz, H-Ar), 8.10 (1 H, t, J = 5.6 Hz, NHCO), 8.46 (1 H, br t, NHCO). 13C NMR (100 MHz, DMSO-d 6): δ = 28.94, 41.90, 42.0, 44.42, 52.46, 53.68, 55.8, 62.52, 73.51, 126.80, 127.01, 127.05, 128.27, 128.4, 128.6, 131.12, 132.03, 138.97, 139.50, 139.7, 167.46, 172.78, 204.45.
  • 22 Kingsbury CA. Egan RA. Perun TJ. J. Org. Chem. 1970; 35: 2913
  • 23 Pandiarajan K. Sabapathy Mohan R. Gomathi R. Muthukumaran G. Magn. Reson. Chem. 2005; 43: 430
    • 25a Kingsbury CA. Egan RA. Perun TJ. J. Org. Chem. 1970; 35: 2913
    • 25b Rabe P. Justus Liebigs Ann. Chem. 1904; 332: 1
    • 25c Rabe P. Elze F. Justus Liebigs Ann. Chem. 1902; 323: 83
    • 26a Kadutskii A. Kozlov N. Russ. J. Org. Chem. 2006; 42: 855
    • 26b Kadutskii AP. Kozlov NG. Synlett 2006; 3349
    • 27a Quiroga J. Mejía D. Insuasty B. Abonía R. Nogueras M. Sánchez A. Cobo J. Low JN. Tetrahedron 2001; 57: 6947
    • 27b Tratrat C. Giorgi-Renault S. Husson H.-P. Org. Lett. 2002; 4: 3187
    • 27c Kadutskii A. Kozlov N. Russ. J. Org. Chem. 2006; 42: 1388
    • 28a Dzvinchuk I. Tolmacheva N. Chem. Heterocycl. Compd. 2001; 37: 506
    • 28b Chebanov V. Saraev V. Desenko S. Orlov V. Gura E. Chem. Heterocycl. Compd. 2004; 40: 475
  • 29 Kozlov NG. Kadutskii AP. Tetrahedron Lett. 2008; 49: 4560
    • 30a Kato T. Yamamoto Y. Sakamoto T. Yakugaku Zasshi 1970; 90: 1400
    • 30b Kato T. Yamamoto Y. Chem. Pharm. Bull. 1965; 13: 959
    • 30c Oda R. Takashima S. Okano M. Bull. Chem. Soc. Jpn. 1962; 35: 1843