Synthesis of Nitrogen- and Oxygen-Containing Heterocycles by Prins Cyclization in Continuous Flow

Abstract

Aza-silyl-Prins and oxa-Prins cyclization reactions in continuous-flow chemistry are described for the synthesis of the corresponding tetrahydropyridines and pyran derivatives, respectively. In particular, the use of pyridine-carboxaldehydes for aza-silyl-Prins reaction led to either a symmetrical triarylmethane or two new bicyclic compounds. 4-Fluorinated-2-substituted tetrahydropyran derivatives were also obtained in the oxa-Prins cyclization with good selectivity in favor of the anti-isomer.

Key words

aza-silyl-Prins - oxa-Prins - continuous-flow chemistry - tetra­hydropyridine - dihydropyran

Publication History

Received: 04 September 2020

Accepted after revision: 09 November 2020

Article published online:
07 December 2020

• References


For reviews and recent publications, see:
• 1a Olier C, Kaafarani M, Gastaldi S, Bertrand MP. Tetrahedron 2010; 66: 413
• 1b Greco SJ, Fiorot RG, Lacerda VJ, Bezerra dos Santos R. Aldrichimica Acta 2013; 46: 59
• 1c Han X, Peh GR, Floreancig PE. Eur. J. Org. Chem. 2013; 1193
• 1d Pastor IM, Yus M. Curr. Org. Chem. 2017; 17: 925
• 1e Subba Reddy BV, Nair PN, Antony A, Lalli C, Grée R. Eur. J. Org. Chem. 2017; 1805
• 1f Katamura T, Shimizu T, Mutoh Y, Saito S. Org. Lett. 2017; 19: 266
• 1g Lu Z, Bajwa BS, Otome OE, Hammond GB, Xu B. Green Chem. 2019; 21: 2224
• 1h Padmaja P, Narayana Reddy P, Subba Reddy BV. Org. Biomol. Chem. 2020; 18: 7514
• 1i Kamakura D, Todoroki H, Urabe D, Hagiwara K, Inoue M. Angew. Chem. Int. Ed. 2020; 59: 479
• 1j Zhang H, He H, Gao S. Angew. Chem. Int. Ed. 2020; 59: 20417
• 2a Carballo RM, Valdomir G, Purino M, Martín VS, Padrón JI. Eur. J. Org. Chem. 2010; 2304
• 2b Bondalapati S, Reddy UC, Kundu DS, Saikia AK. J. Fluorine Chem. 2010; 131: 320
• 2c Subba Reddy BV, Borkar P, Chakravarthy PP, Yadav JS, Gree R. Tetrahedron Lett. 2010; 51: 3412
• 2d Chio FK, Warne J, Gough D, Penny M, Green S, Coles SJ, Hursthouse MB, Jones P, Hassall L, McGuire TM, Dobbs AP. Tetrahedron 2011; 67: 5107
• 3a Cloninger MJ, Overman LE. J. Am. Chem. Soc. 1999; 121: 1092
• 3b Barry CS. J, Crosby SR, Harding JR, Hughes RA, King CD, Parker GD, Willis CL. Org. Lett. 2003; 5: 2429
• 3c Yadav JS, Reddy MS, Rao PP, Prasad AR. Tetrahedron Lett. 2006; 47: 4397
• 3d Yadav JS, Krishana GG, Kumar SN. Tetrahedron 2010; 66: 480
• 3e Vintonyak VV, Maier ME. Org. Lett. 2008; 10: 1239
• 4a Yadav JS, Subba Reddy BV, Kumar GG. K. S. N, Reddy GM. Chem. Lett. 2007; 36: 426
• 4b Miranda PO, Carballo RM, Martín VS, Padrón JI. Org. Lett. 2009; 11: 357
• 4c Rychnovsky SD, Yang G, Hu Y, Khire UR. J. Org. Chem. 1997; 62: 3022
• 5a Dobbs AP, Martinović S. Tetrahedron Lett. 2002; 43: 7055
• 5b Dobbs AP, Guesné SJ. J, Martinović S, Coles SJ, Hursthouse MB. J. Org. Chem. 2003; 68: 7880
• 5c Dobbs AP, Guesné SJ. J, Hursthouse MB, Coles SJ. Synlett 2003; 1740
• 5d Díez-Poza C, Barbero H, Diez-Varga A, Barbero A. In Progress in Heterocyclic Chemistry, Vol. 30. Gribble GW, Joule JA. Elsevier; London: 2018: 13
• 5e Diez-Poza C, Fernandez-Peña L, Cherubin A, Lion-Villar J, Barbero A. ARKIVOC 2020; (i): 96
• 6a Kishi Y, Nagura H, Inagi S, Fuchigami T. Chem. Commun. 2008; 3876
• 6b Kishi Y, Inagi S, Fuchigami T. Eur. J. Org. Chem. 2009; 103
• 6c Batista PK, Ferreira JM. G. de O, Silva FP. L, Vasconcellos ML. A. A, Vale JA. Molecules 2019; 24: 2084
• 6d Wang W, Shao L, Cheng W, Yang J, He M. Catal. Commun. 2008; 9: 337
• 7a Launay GG, Slawin AM. Z, O’Hagan D. Beilstein J. Org. Chem. 2010; 6: 41
• 7b Parchinsky V, Shumsky A, Krasavin M. Tetrahedron Lett. 2011; 52: 7157
• 7c Parchinsky V, Shumsky A, Krasavin M. Tetrahedron Lett. 2011; 52: 7161
• 8 Hirai K, Takeda R, Hutchison JA, Uji-i H. Angew. Chem. Int. Ed. 2020; 59: 5332 ; Angew. Chem. 2020, 132, 5370
• 9a Hughes DL. Org. Process Res. Dev. 2018; 22: 13
• 9b Akwi FM, Watt P. Chem. Commun. 2018; 54: 13894
• 9c Bogdan AR, Organ MG. In Top. Heterocycl. Chem., Vol. 56. Sharma UK, van der Eycken EV. Springer; Cham: 2018: 319
• 9d Brandão P, Pineiro M, Pinho e Melo TM. V. D. Eur. J. Org. Chem. 2019; 7188
• 10a Bagley MC, Fusillo V, Jenkins RL, Lubinu MC, Mason C. Beilstein J. Org. Chem. 2013; 9: 1957
• 10b Tambarussi BP, Noël T, Wang Q, Hessel V. Tetrahedron Lett. 2014; 55: 2090
• 10c Martin RE, Morawitz F, Kuratli C, Alker AM, Alanine AI. Eur. J. Org. Chem. 2012; 47
• 11a Giovine A, Musio B, Degennaro L, Falcicchio A, Nagaki A, Yoshida J.-i, Luisi R. Chem. Eur. J. 2013; 19: 1873
• 11b Tsoung J, Bogdan AR, Kantor S, Wang Y, Charaschanya M, Djuric SW. J. Org. Chem. 2017; 82: 1073
• 12a Baumann M, Baxendale IR, Kirschning A, Ley SV, Wegner J. Heterocycles 2011; 82: 1297
• 12b Drop M, Bantreil X, Grychowska K, Mahoro GU, Colacino E, Pawłowski M, Martinez J, Subra G, Zajdel P, Lamaty F. Green Chem. 2017; 19: 1647
• 13a Osorio-Planes L, Rodríguez-Escricha C, Pericàs MA. Catal. Sci. Technol. 2016; 6: 4686
• 13b Riva E, Rencurosi A, Gagliardi S, Passarella D, Martinelli M. Chem. Eur. J. 2011; 17: 6221
• 14a York M. Tetrahedron Lett. 2011; 52: 6267
• 14b Fukuyama T, Fujita Y, Rashid MA, Ryu I. Org. Lett. 2016; 18: 5444
• 14c Hoffmeyer P, Schneider C. Eur. J. Org. Chem. 2019; 5326
• 15a Dobbs AP, Guesné SJ. J. Synlett 2005; 2101
• 15b Colin O, Greck C, Prim D, Thomassigny C. Eur. J. Org. Chem. 2014; 7000
• 15c Subba Reddy BV, Chaya DN, Yadav JS, Grée R. Synthesis 2012; 44: 297
• 16 Kazuo K, Tsutomu K, Junji M. PTC Int. Apl WO 2010131717, 2010
• 17a Wang X, Wang Y, Du D.-M, Xu J. J. Mol. Catal. A: Chem. 2006; 255: 31
• 17b Harikrishnan A, Gnanasekaran R, Ramanathan CR. ChemistrySelect 2016; 1: 3022
• 18a Jaber JJ, Mitsui K, Rychnovsky SD. J. Org. Chem. 2001; 66: 4679
• 18b Okoromoba OE, Hammond GB, Xu B. Org. Lett. 2015; 17: 3975
• 19 Yoshida J, Ishichi Y, Isoe S. J. Am. Chem. Soc. 1992; 114: 7594