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Synthesis 2016; 48(08): 1226-1234
DOI: 10.1055/s-0035-1561355
DOI: 10.1055/s-0035-1561355
paper
Synthesis of Novel Hydroxymethyl-Substituted Fused Heterocycles
Further Information
Publication History
Received: 17 December 2015
Accepted after revision: 08 January 2016
Publication Date:
18 February 2016 (online)
◊ Current address: AstraZeneca R&D, Darwin Building (310), Cambridge Science Park, Milton Road, Cambridge, CB4 0WG, UK
Abstract
Examples of hydroxymethylated analogues of heteroaryl cores such as quinazolin-4-ones, isoquinolin-1(2H)-ones, pyrido[3,4-d]pyrimidin-4(3H)-ones, chromen-4-ones and pyrrolo[2,1-f][1,2,4]triazin-4(3H)-ones are sparse or non-existent in the scientific literature. We have demonstrated that such compounds are accessible by using standard procedures from readily available raw materials.
Key words
cross-coupling - fused-ring systems - heterocycles - quinazolinones - isoquinolinones - chromenones - triazinonesSupporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0035-1561355.
- Supporting Information
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References
- 1 Horton DA, Bourne GT, Smythe ML. Chem. Rev. 2003; 103: 893
- 2 Johannes JW, Almeida L, Barlaam B, Boriack-Sjodin PA, Casela R, Croft RA, Dishington AP, Gingipalli L, Gu C, Hawkins JL, Holmes JL, Howard T, Huang J, Ioannidis S, Kazmirski S, Lamb ML, McGuire TM, Moore J, Ogg D, Patel A, Pike KG, Pontz T, Robb G, Su N, Wang H, Wu X, Zhang H, Zhang Y, Zheng X, Wang W. ACS Med. Chem. Lett. 2015; 6: 254
- 3a Wolfe JF, Rathman TL, Sleevi MC, Campbell JA, Greenwood TD. J. Med. Chem. 1990; 33: 161
- 3b Tripathi LM, Tekwani BL. Sen G, Ghatak S. Indian J. Exp. Biol. 1985; 23: 452
- 4 De Laszlo SE, Quagliato CS, Greenlee WJ, Patchett AA, Chang RS. L, Lotti VJ, Chen TB, Scheck SA, Faust KA. J. Med. Chem. 1993; 36: 3207
- 5a Pendergast W, Johnson JV, Dickerson SH, Dev IK, Duch DS, Ferone R, Hall WR, Humphreys J, Kelly JM, Wilson DC. J. Med. Chem. 1993; 36: 2279
- 5b Kung PP, Casper MD, Cook KL, Wilson-Lingardo L, Risen LM, Vickers TA, Rankin R, Blyn LB, Wyatt JR, Cook PD. J. Med. Chem. 1999; 42: 4705
- 6a Chern JW, Tao PL, Wang KC, Gutcait A, Liu SW, Yen MH, Chien SL, Rong JK. J. Med. Chem. 1998; 41: 3128
- 6b Hirai S, Kikuchi H, Kim H.-S, Begum K, Watay Y, Tasaka H, Miyazawa Y, Yamamoto K, Oshima Y. J. Med. Chem. 2003; 46, 4351
- 6c Kikuchi H, Tasaka H, Hirai S, Takaya Y, Iwabuchi Y, Ooi H, Hatakeyama S, Kim H.-S, Wataya Y, Oshima Y. J. Med. Chem. 2002; 45: 2563
- 7 Ravn C, Rasmussen SR. PCT Int. Appl. WO2006002255, 2006 ; Chem. Abstr. 2006, 144, 94418.
- 8a Segarra V, Crespo MI, Pujol F, Beleta J, Domenech T, Miralpeix M, Palacios JM, Castro A, Martinez A. Bioorg. Med. Chem. Lett. 1998; 8: 505
- 8b Connelly DJ, Guiry PJ. Synlett 2001; 1707
- 8c Liu JF, Ye P, Zhang B, Bi G, Sargent K, Yu L, Yohannes D, Baldino CM. J. Org. Chem. 2005; 70: 6339
- 8d Kshirshagar UA, Agarde NP. Org. Lett. 2010; 12: 3716
- 9a Xu L, Jiang Y, Ma D. Org. Lett. 2012; 14: 1150
- 9b Zhou J, Fu L, Lv M, Liu J, Pei D. Ding K. 2008; 15: 3974
- 9c Liu X, Fu H, Jiang Y, Xhao Y. Angew. Chem. Int. Ed. 2009; 48: 348 ; Angew. Chem. 2009, 121, 354
- 10a Cox CD, Raheem IT, Flores BA, Whitman DB. US Pat. Appl. Publ. US20110319409, 2011 ; Chem. Abstr. 2011, 156, 92460.
- 10b Dumaître B, Dodic N. J. Med. Chem. 1996; 39: 1635
- 10c Nara H, Sato K, Naito T, Motokani H, Oki H, Yamamoto Y, Kuno H, Santou T, Kanzaki N, Terauchi J, Uchikawa O, Kori M. Bioorg. Med. Chem. 2014; 22: 5487
- 11 Threadgill MD, Lloyd MD, Thompson AS, Nathubai A, Wood PJ, Paine HA, Kumpan E, Sunderland PT, Chie Yen Woon E. PCT Int. Appl. WO2014087165, 2014 ; Chem. Abstr. 2014, 161, 99203.
- 12a Audoux J, Ple N, Turck A, Queguinner G. Tetrahedron 2004; 60: 4107
- 12b Kanuouni T, Stafford JA, Veal AM, Wallace MB. PCT Int. Appl. WO2014151106, 2014 ; Chem. Abstr. 2014, 161, 535601.
- 13 Bakke JM, Riha J. J. Heterocycl. Chem. 2001; 38: 99
- 14 Chen J, Wu D, He F, Liu M, Wu H, Ding J, Su W. Tetrahedron Lett. 2008; 49: 3814
- 15 Klein B, Berkowitz J, Hetman NE. J. Org. Chem. 1961; 26: 126
- 16a Jin Y, Khadka DB, Yang SH, Zhao C, Cho W-J. Tetrahedron Lett. 2014; 55: 1366
- 16b Van H TM, Woo H, Jeong HM, Khadka DB, Yang SH, Zhao C, Jin Y, Lee E.-S, Lee KY, Kwon Y, Cho W.-J. Eur. J. Med. Chem. 2014; 82: 181
- 16c Ueno K, Sasaki A, Kawano K, Okabe T, Kitazawa N, Takahasi K, Yamamoto N, Suzuki Y, Matsunaga M, Kubota A. PCT Int. Appl. WO9918977, 1999 ; Chem. Abstr. 1999, 130, 311813.
- 17 Marsden SP, Raw SA, Webb NJ. Org. Lett. 2014; 16: 4718
- 18 Wang H, Grohmann C, Nimphius C, Glorius F. J. Am. Chem. Soc. 2012; 134: 19592
- 19 Masakazu F, Hiroyuki S, Atsushi N, Shinichi T, Yasuhiro E, Ryou T. PCT Int. Appl. WO2002094790, 2002 ; Chem. Abstr. 2002, 138, 4615.
- 20 Briet P, Berthelon J.-J, Collonges F. EP80419, 1983 ; Chem. Abstr. 1983, 99, 122305.
- 21a Chen Y, Xiang H, Tan C, Xie Y, Yang C. Tetrahedron 2013; 69: 2714
- 21b Sampognaro AJ, Wittman MD. PCT. Int. Appl. WO2008131050, 2008 ; Chem. Abstr. 2008, 149, 513870.
- 22 Sampognaro AJ, Wittman MD, Carboni JM, Chang C, Greer AF, Hurlburt WW, Sack JS, Vyas DM. Bioorg. Med. Chem. Lett. 2010; 20: 5027