Tandem Ring-Opening/Closing Reactions ofN-Ts Aziridines and Aryl Propargyl Alcohols Promoted byt-BuOK
作者： Liang Wang , Qi-Bin Liu , Duo-Sheng Wang , Xin Li , Xiu-Wen Han
DOI: 10.1021/OL802862P
关键词:
摘要: t-BuOK was found to be an effective promoting reagent for tandem ring-opening/closing reactions of various N-Ts aziridines and aryl propargyl alcohols afford dihydroxazine derivatives in moderate good yields. A plausible reaction mechanism has been proposed.
acs.org
irgrid.ac.cn参考文章(57)
Muhammad Yar, Eoghan M. McGarrigle, Varinder K. Aggarwal, An Annulation Reaction for the Synthesis of Morpholines, Thiomorpholines, and Piperazines from β-Heteroatom Amino Compounds and Vinyl Sulfonium Salts Angewandte Chemie. ,vol. 47, pp. 3784- 3786 ,(2008) , 10.1002/ANIE.200800373
Nitya G. Kundu, Gopeswar Chaudhuri, Anup Upadhyay, Palladium-Catalyzed Heteroannulation Leading to Heterocyclic Structures with Two Heteroatoms: A Highly Regio- and Stereoselective Synthesis of (Z)-4-Alkyl-2-alkyl(aryl)idene-3,4-dihydro-2H-1,4-benzoxazines and (Z)-3-Alkyl(aryl)idene-4-tosyl-3,4-dihydro-2H-1,4-benzoxazines† Journal of Organic Chemistry. ,vol. 66, pp. 20- 29 ,(2001) , 10.1021/JO000826J
Karin Leijondahl, Linnéa Borén, Roland Braun, Jan-E. Bäckvall, Enantiopure 1,5-Diols from Dynamic Kinetic Asymmetric Transformation. Useful Synthetic Intermediates for the Preparation of Chiral Heterocycles Organic Letters. ,vol. 10, pp. 2027- 2030 ,(2008) , 10.1021/OL800468H
Tianning Diao, Xiaoyu Sun, Renhua Fan, Jie Wu, Unexpected Ring-opening Reaction of Aziridine with Acetic Anhydride in DMF Chemistry Letters. ,vol. 36, pp. 604- 605 ,(2007) , 10.1246/CL.2007.604
Devarajulu Sureshkumar, Srinivasa Murthy Koutha, Srinivasan Chandrasekaran, Chemistry of tetrathiomolybdate: aziridine ring opening reactions and facile synthesis of interesting sulfur heterocycles. Journal of the American Chemical Society. ,vol. 127, pp. 12760- 12761 ,(2005) , 10.1021/JA052969Z
Toshiro Ibuka, THE AZA-PAYNE REARRANGEMENT : A SYNTHETICALLY VALUABLE EQUILIBRATION Chemical Society Reviews. ,vol. 27, pp. 145- 154 ,(1998) , 10.1039/A827145Z
Fu-Qiang Shi, Xin Li, Yuanzhi Xia, Liming Zhang, Zhi-Xiang Yu, DFT study of the mechanisms of in water Au(I)-catalyzed tandem [3,3]-rearrangement/Nazarov reaction/[1,2]-hydrogen shift of enynyl acetates: a proton-transport catalysis strategy in the water-catalyzed [1,2]-hydrogen shift. Journal of the American Chemical Society. ,vol. 129, pp. 15503- 15512 ,(2007) , 10.1021/JA071070+
Qing-Gang Wang, Xian-Ming Deng, Ben-Hu Zhu, Long-Wu Ye, Xiu-Li Sun, Chuan-Ying Li, Chun-Yin Zhu, Qi Shen, Yong Tang, Tandem Michael addition/ylide epoxidation for the synthesis of highly functionalized cyclohexadiene epoxide derivatives. Journal of the American Chemical Society. ,vol. 130, pp. 5408- 5409 ,(2008) , 10.1021/JA800747M
Liansuo Zu, Jian Wang, Hao Li, Hexin Xie, Wei Jiang, Wei Wang, Cascade Michael--aldol reactions promoted by hydrogen bonding mediated catalysis. Journal of the American Chemical Society. ,vol. 129, pp. 1036- 1037 ,(2007) , 10.1021/JA067781+
Jie Wu, Xiaoyu Sun, Yizhe Li, DABCO: An Efficient Organocatalyst in the Ring‐Opening Reactions of Aziridines with Amines or Thiols European Journal of Organic Chemistry. ,vol. 2005, pp. 4271- 4275 ,(2005) , 10.1002/EJOC.200500576