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Acid and 1, 2‐Dichloroethane Co‐Promoted Substitution of the Amino Groups in Gramine and its Analogues with Trialkyl Phosphites
Author(s) -
Guo Shengmei,
Zhang Zhebin,
Xu Jianxin,
Li Sen,
Fu Zhengjiang,
Cai Hu
Publication year - 2019
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201904138
Subject(s) - chemistry , reagent , alkylation , phosphine , nucleophilic substitution , catalysis , medicinal chemistry , organic chemistry , nucleophile , substitution reaction , primary (astronomy) , physics , astronomy
The transformation of gramine and its analogues represents an important strategy in organic chemistry. Here, we report an acid and DCE co‐promoted phosphonation of gramine and its analogues using trialkyl phosphites as nucleophilic reagents. This reaction avoided the use of stoichiometric alkylation reagents, PBu 3 (Tributyl phosphine) and noble metal catalyst. Except for the tertiary amino group in indoles, the primary amino and secondary amino groups, which the previous work did not mentioned were explored.