Sustainable alternative protocols for the multicomponent synthesis of spiro-4H-pyrans catalyzed by 4-dimethylaminopyridine

Masoumeh Zakeri; Mohamed Mahmoud Nasef; Ebrahim Abouzari-Lotf; Arezoo Moharami; Majid M. Heravi

Journal of Industrial and Engineering Chemistry, Vol.29, 273-281, September, 2015

DOI10.1016/j.jiec.2015.03.035 Export Citation

Sustainable alternative protocols for the multicomponent synthesis of spiro-4H-pyrans catalyzed by 4-dimethylaminopyridine

Masoumeh Zakeri^{1, †}, Mohamed Mahmoud Nasef^{1, 2, †}, Ebrahim Abouzari-Lotf², Arezoo Moharami³, and Majid M. Heravi³

¹Malaysia–Japan International Institute of Technology, International Campus, Universiti Teknologi Malaysia, Kuala Lumpur, 54100, Malaysia
²Advanced Materials Research group, Institute of Hydrogen Economy, Universiti Teknologi Malaysia, International Campus, Jalan Semarak, Kuala Lumpur, 54100, Malaysia
³Department of Chemistry, School of Sciences, Alzahra University, Vanak, Tehran, Iran

E-mail:,

Green approaches to the synthesis of spiro-4H-pyrans are reported based on the one-pot and three-component condensation via a domino Knoevenagel/Michael/cyclization sequence. These approaches involve evaluation of the activity of several organocatalysts in water as a reaction media and also under solvent-free in both microwave irradiation and ball milling conditions. Extensive experiments were carried out to optimize the reaction parameters including type and amount of catalyst, reaction temperature and time. Microwave irradiation in presence of 4-dimethylaminopyridine (DMAP) was observed as the best procedure with good yields, short reaction time, environmental friendliness, and convenient operation.

Keywords:Green chemistry;Microwave irradiation;Ball milling;Spiro-4H-pyrans;4-Dimethylaminopyridine

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[Referenced By]

[1] Lindstrom UM, Organic Reactions in Water: Principles, Strategies and Applications, John Wiley & Sons, London, 2007p. 1.

[2] Bruckmann A, Krebs A, Bolm C, Green Chem., 10, 1131 (2008)

[3] Varma RS, Green Chem., 1, 43 (1999)

[4] Perreux L, Loupy A, Tetrahedron, 57, 9199 (2001)

[5] Singh MS, Chowdhury S, RSC Adv., 2, 4547 (2012)

[6] Nazari S, Ghandi K, J. Ind. Eng. Chem., 21, 198 (2015)

[7] Zhang Z, Wu HH, Tan YJ, RSC Adv., 3, 16940 (2013)

[8] Ferguson M, Giri N, Huang X, Apperley D, James SL, Green Chem., 16, 1374 (2014)

[9] Stolle A, Szuppa T, Leonhardt SES, Ondruschka B, Chem. Soc. Rev., 40, 2317 (2011)

[10] Wang GW, Chem. Soc. Rev., 42, 7668 (2013)

[11] Galliford CV, Scheidt KA, Angew. Chem.-Int. Edit., 46, 8748 (2007)

[12] Williams RM, Cox RJ, Acc. Chem. Res., 36, 127 (2002)

[13] Onishi T, Sebahar PR, Williams RM, Tetrahedron, 60, 9503 (2004)

[14] Onishi T, Sebahar PR, Williams RM, Org. Lett., 5, 3135 (2003)

[15] Wang H, Ganesan A, J. Org. Chem., 65, 4685 (2000)

[16] Kumar A, Gupta G, Srivastava S, Bishnoi AK, Saxena R, Kant R, Khanna RS, Maulik PR, Dwivedi A, RSC Adv., 3, 4731 (2013)

[17] Yu B, Yu DQ, Liu HM, Eur. J. Med. Chem., http://dx.doi.org/10.1016/j.ejmech.2014.06.056. (2014)

[18] Crespo A, El Maatougui A, Biagini P, Azuaje J, Coelho A, Brea J, Loza MI, Cadavid MI, Garcıa-Mera X, Gutierrez-de-Teran H, Sotelo E, ACS Med. Chem. Lett., 4, 1031 (2013)

[19] Ghahremanzadeh R, Rashid Z, Zarnani AH, Naeimi H, J. Ind. Eng. Chem., 20(6), 4076 (2014)

[20] Hari GS, Lee YR, Synthesis, 010, 453 (2010)

[21] Li Y, Chen H, Shi C, Shi D, Ji S, J. Comb. Chem., 12, 231 (2010)

[22] Shanthi G, Subbulakshmi G, Perumal PT, Tetrahedron, 63, 2057 (2007)

[23] Wang LM, Jiao N, Qiu J, Yu JJ, Liu JQ, Guo FL, Liu Y, Tetrahedron, 66, 339 (2010)

[24] Mobinikhaledi A, Foroughifar N, Fard MAB, Synth. Commun., 41, 441 (2011)

[25] Kidwai M, Jahan A, Mishra NK, Appl. Catal. A: Gen., 425-426, 35 (2012)

[26] Rad-Moghadam K, Youseftabar-Miri L, Tetrahedron, 67, 5693 (2011)

[27] Chen WB, Wu ZJ, Pei QL, Cun LF, Zhang XM, Yuan WC, Org. Lett., 12, 3132 (2010)

[28] Brahmachari G, Das S, RSC Adv., 4, 7380 (2014)

[29] Aleman J, Cabrera S, Chem. Soc. Rev., 42, 774 (2013)

[30] Rai P, Srivastava M, Singh J, Singh J, RSC Adv., 3, 18775 (2013)

[31] Hofle G, Steglich W, Vorbruggen H, Angew. Chem.-Int. Edit., 17, 569 (1978)

[32] Berry DJ, DiGiovanna CV, Metrick, Murugan S, Arkivok, 201 (2001)

[33] Heravi MM, Zakeri M, Mohammadi N, Chin. J. Chem., 29, 1163 (2011)

[34] Heravi MM, Zakeri M, Pooremamy S, Oskooie HA, Synth. Commun., 41, 113 (2010)

[35] Heravi M, Zakeri M, Moharami A, J. Chem. Sci., 124, 865 (2012)

[36] Bordwell FG, Acc. Chem. Res., 21, 456 (1988)

[37] Karimi AR, Sedaghatpour F, Synthesis, 010, 1731 (2010)

[38] Saluja P, Aggarwal K, Khurana JM, Synth. Commun., 43, 3239 (2013)

[39] Zhu SL, Ji SJ, Zhang Y, Tetrahedron, 63, 9365 (2007)

[40] Sridhar BSR, Bandaru M, Vutukuri PR, Yadavalli VDN, Kakulapati RR, Can. J. Chem., 87, 1704 (2009)

[41] Baharfar R, Azimi R, Synth. Commun., 44, 89 (2013)