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Synthesis and reactivity of pyrrolo[1,2‐α]quinoxalines. Crystal structure and AM1 calculation
Author(s) -
Blache Yves,
Gueiffier Alain,
Elhakmaoui Ahmed,
Viols Henri,
Chapat JeanPierre,
Chavig Olivier,
Teulade JeanClaude,
Grassy Gérard,
Dauphin Gérard,
Carpy Alain
Publication year - 1995
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.5570320437
Subject(s) - chemistry , monoclinic crystal system , reactivity (psychology) , yield (engineering) , condensation , crystal structure , condensation reaction , surface modification , group (periodic table) , medicinal chemistry , stereochemistry , crystallography , combinatorial chemistry , organic chemistry , catalysis , medicine , materials science , alternative medicine , physics , pathology , metallurgy , thermodynamics
2‐Methylquinoxaline reacts with ethyl bromopyruvate giving 2‐substituted pyrrolo[1,2‐α]quinoxalines. The yield of the condensation depends on the functionalization of starting materials, and optimization is obtained with 2‐dimethylamino‐3‐methylquinoxaline ( 1c ). Reactivity of the resulting pyrrolo[1,2‐a]‐quinoxalines was investigated and supported by a theoretical approach (AM1 calculation performed with the MOPAC 6.0 software). X‐ray analysis of 5 which crystallizes in the monoclinic system, space group P2 1 /n, with a = 9.095(1), b = 8.972(1), c = 17.749(3) A, β = 96.56(1)°, is also reported.
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