Cycloaddition of 1-azirines to 1,2,4,5-tetrazines. Synthesis and rearrangement of 1,2,4-triazepines

David J. Anderson, Alfred Hassner

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Abstract

Thermal 1 : 1 cycloaddition of 1-azirines to sym-tetrazines provides a synthesis of the as yet unknown class of 1,2,4-triazepines and also leads via these intermediates to pyrimidines, pyrazoles, and 2 : 1 adducts.

Original languageEnglish
Pages (from-to)45b-46
JournalChemical Communications
Issue number2
DOIs
StatePublished - 1974
Externally publishedYes

Bibliographical note

Funding Information:
Analogy for these observations is found3 in the formation of pyridines and pyrazoles from lH-1,Z-diaze- R' R3 Since reaction of the triazepine (4b) with excess of the + R30 + 2:l Adduct (-N,-MeCN) pines. azirine (2b) afforded the 2: 1adduct (Sc),it is possible that N the adducts (8) possess a triazocine structure, formed viaH (8) cycloaddition of a further molecule of azirine to either the triazepine (4) or a bicyclic isomer,6 followed by extrusion of 12(a)R=R3 =Ph,R=Me MeCN. 3 1 2 3 Support of this research by a Grant from the National (b)RLPh,R=p-ToL (b)R,=Ph,R=Me,R=p-Tol Cancer Institute is acknowledged. 2 3 (c)RLP~,R%~-P~ (c)R=Ph,R=MeJR=2-Py (Received,4th September 1973; Cam.

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