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Molecular design of heterocycles. 2. “Structure-synthesis” magic rule in the synthesis of six-membered heteroaromatic rings (review)

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

This review deals with the frequency of occurrence of literature references to various types of reagents used in syntheses of the pyridine ring and a number of its heterocyclic analogs (classed as heteroalternant systems). It is shown that the nature of the terminal groups in the reagents, the parity of the chain of atoms between the terminal groups, and the position of the heteroatom are interrelated and are subject to “magic” rules (principles of alternation and heteroalternation). These rules can be interpreted within the frame of a new concept, “structure—synthesis,” based on preservation of the electrophilic-nucleophilic nature of the reagents in the heterolytic formation of even-membered rings. A complete classification of pyridine-ring syntheses that are allowed by the rules provides a means for predicting the polar type of reagents for the last unknown synthesis of pyridines of the type CNCCC+C.

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Authors and Affiliations

  1. Chemistry Department, M. V. Lomonosov Moscow State University, 119899, Moscow

    E. V. Babaev

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This article is dedicated to Prof. A. R. Katritsky on the occasion of his 65th birthday.

See [1] for Communication 1.

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 7, 937–961, July, 1993.

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Babaev, E.V. Molecular design of heterocycles. 2. “Structure-synthesis” magic rule in the synthesis of six-membered heteroaromatic rings (review). Chem Heterocycl Compd 29, 796–817 (1993). https://doi.org/10.1007/BF00528890

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  • DOI: https://doi.org/10.1007/BF00528890

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