Synthesis of 1,4-Diazacycles by Hydrogen Borrowing

10.1021/jm501100b aCyclizine. https://en.wikipedia.org/wiki/Cyclizine (accessed 2022-05-01). bCetirizine. https://pubchem.ncbi.nlm.nih.gov/compound/Cetirizine (accessed 2022-05-01). cSitagliptin. https://en.wikipedia.org/wiki/Sitagliptin (accessed 2022-05-01). aHomochlorcyclizine. https://en.wikipedia.org/wiki/Homochlorcyclizine (accessed 2022-05-01). bHomofenazine. https://pubchem.ncbi.nlm.nih.gov/compound/Homofenazine (accessed 2022-05-01). 10.1055/s-0036-1589491 10.1039/D0MD00053A aKono, S.; Watanabe, H. Homopiperazine from N,N′-Dibenzylethylenediamine. JP43023629, 1968. bSun, J.; Wu, X.; Zhang, F. A Process for Preparing Homopiperazine. CN101891692, 2010. cLiu, H. Process for the Preparation of Pharmaceutical Intermediate Homopiperazine Using Amino Potection and Cyclization Reaction. CN103360330, 2013. aLu, J.; Wang, S.; Lu, X.; Zou, Z. Process for Preparation of N-Monosubstituted Homopiperazine. CN103121976, 2013. aGao, J.; Wang, X.; Li, Y.; Ye, D.; Xie, C. A Process for Preparing Homopiperazine and its Derivative. CN102120732, 2011. 10.1021/jo502688b 10.1021/jo900441s 10.1021/acs.orglett.5b03708 10.1038/s41467-018-03085-3 10.1021/ol300030w 10.1248/yakushi1947.79.2_153 10.1038/nchem.1878 10.1002/ejoc.201403261 10.1016/j.tetlet.2006.07.033 10.1007/s11144-012-0447-z 10.1021/acscatal.6b03088 10.1021/acs.orglett.0c01485 10.1021/acscatal.6b00175 10.1002/ejoc.201201099 10.1039/C9CC03975A Shimazu, H. Preparation of Homopiperazine from 1,3-Diaminopropane and Ethylene Glycol. JP2006306790, 2006. 10.1021/acs.oprd.5b00199 10.1016/S0960-894X(02)01034-X 10.1021/acs.jmedchem.6b01868 Barth, R.; Höferl-Prantz, K.; Richter, F.; Widschwenter, G. Novel Routes of Synthesis for the Preparation of Suvorexant. WO 2016020405 A1, 2016. 10.1586/17512433.2014.966813 10.1021/jo8010655 10.1039/b712685a 10.1021/acscatal.7b02817 10.1021/cr9003133