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Preparation, X‐ray crystal structure and 13 C‐ and 1 H‐NMR study of 1‐methyl‐2‐( N ‐methyl‐ N ‐phenylglycyl)‐3‐( N ‐methylanilino)indole
Author(s) -
Farfán Norberto,
Hernández J. Manuel,
JosephNathan Pedro,
Contreras Rosalinda
Publication year - 1990
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570270644
Subject(s) - triclinic crystal system , chemistry , crystal structure , heteronuclear molecule , homonuclear molecule , crystallography , yield (engineering) , carbon 13 nmr , nmr spectra database , x ray crystallography , indole test , stereochemistry , nuclear magnetic resonance spectroscopy , spectral line , diffraction , molecule , organic chemistry , materials science , physics , astronomy , optics , metallurgy
Reaction of N ‐methylaniline with 40% glyoxal yields 1‐methyl‐2‐( N ‐methyl‐ N ‐phenylglycyl)‐3‐( N ‐methylanilino)indole ( 1a ) as the main product together with 1‐methyl‐3‐( N ‐methylanilino)indole ( 1b ). The reaction appears to be general for aromatic secondary amines since N ‐ethylaniline and N ‐phenylbenzylamine yield the corresponding indoles. The structure of 1a has been verified by single crystal X‐ray diffraction. Compound 1a (C 25 H 25 N 3 O) crystallized in the triclinic space group Pl̄ with cell dimensions a = 10.085(3)Å, b = 10.371(3)Å, c = 11.908(5)Å, α = 74.2(3)°, β = 74.7(3)° and γ = 60.7(2)° with Z = 2. The complete 1 H and 13 C nmr assignment of indoles 1a and 1b was achieved from two‐dimensional HETCOR and COSY spectra with the aid of homonuclear and heteronuclear double resonance experiments.