2-氨基-4H-吡喃在碘苯二乙酸和 N-氯代丁二酰亚胺中的氧化双官能化反应：反应性、机理研究和 DFT 计算。
Oxidative difunctionalization of 2-amino-4H-pyrans in iodobenzene diacetate and N-chlorosuccinimide: reactivity, mechanistic insights, and DFT calculations.
机构信息
Crop Protection Chemicals, CSIR-Indian Institute of Chemical Technology, Tarnaka, Hyderabad 500607, India.
出版信息
J Org Chem. 2012 Dec 7;77(23):10648-54. doi: 10.1021/jo301801b. Epub 2012 Nov 14.
PMID:23130633
Abstract
Oxidative difunctionalization of 2-amino-4H-pyrans was accomplished with iodobenzene diacetate (IBD) and N-chlorosuccinimide (NCS) reagents in alcoholic medium. 2-Amino-4H-pyrans undergo geminal dialkoxylation with the migration of an amino group (1a,b, 2a-i, 3a,b, and 4) in IBD, whereas with NCS addition of both chlorine and alkoxy groups takes place across the chromene double bond (6a-i).
摘要
在醇介质中，用碘苯二乙酸酯（IBD）和 N-氯代丁二酰亚胺（NCS）试剂实现了 2-氨基-4H-吡喃的氧化双官能化。2-氨基-4H-吡喃在 IBD 中经历偕二烷氧基化，同时氨基基团迁移（1a,b, 2a-i, 3a,b 和 4），而与 NCS 加成则在色烯双键上发生氯和烷氧基的加成（6a-i）。
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