Chemistry of Heterocyclic Compounds p. 932 - 937 (1982)
Update date:2022-07-31
Topics:
Daukshas, V. K.
Martinkus, R. S.
Gineitite, V. L.
Urbonene, S. L.
A method for the synthesis of 2-carboxy-5,6-ethylenedioxyindole and its 4- and 7-chloro derivatives from 3,4-ethylenedioxyaniline and, correspondingly, its 2- and 5-chloro derivatives via Fischer reaction was developed.It was established that in the case of bromination or chlorination under mild conditions 2-carbethoxy-5,6-ethylenedioxyindole forms 3-halo derivatives, while 5,6-ethylenedioxyindole itself forms only 3,7-dihalo derivatives.The closeness in the reactivities of the 3 and 7 ring positions of 5,6-ethylenedioxyindole (as compared with indole) is in agreement with the results of calculations of the quantum-chemical reactivity indexes for electrophilic substitution.
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Doi:10.1248/cpb.30.2840
(1982)Doi:10.1016/0008-6215(82)84027-5
(1982)Doi:10.1007/BF00506157
(1982)Doi:10.1016/S0008-6215(00)81888-1
(1982)Doi:10.1246/cl.1982.1579
(1982)Doi:10.1016/S0040-4039(01)91265-1
(1984)
