Synthesis of N-Cycloalkenylazoles

N-(1-Cycloalkenyl)pyrroles 3a,b, -pyrazoles 6a,b, and -imidazoles 9a,b were synthesized via elimination of benzotriazole or 5-phenyltetrazole from the corresponding 1-[1-(heterocycyl)cycloalkyl]benzotriazoles 2, 5, and 8 or 1-[1-(heterocycyl)cyclohexyl]-5-phenyltetrazole (12 and 14). Intermediates 2...

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Veröffentlicht in:	Journal of organic chemistry 2002-11, Vol.67 (23), p.8230-8233
Hauptverfasser:	Katritzky, Alan R, Maimait, Rexiat, Xu, Yong-Jiang, Gyoung, Young Soo
Format:	Artikel
Sprache:	eng
Schlagworte:	Azoles - chemical synthesis Chemistry Exact sciences and technology Heterocyclic compounds Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings Heterocyclic Compounds, 2-Ring - chemical synthesis Heterocyclic Compounds, 3-Ring - chemical synthesis Imidazoles - chemical synthesis Neurons Organic chemistry Preparations and properties Pyrazoles - chemical synthesis Pyrroles - chemical synthesis Wounds and Injuries
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Beschreibung
Zusammenfassung:	N-(1-Cycloalkenyl)pyrroles 3a,b, -pyrazoles 6a,b, and -imidazoles 9a,b were synthesized via elimination of benzotriazole or 5-phenyltetrazole from the corresponding 1-[1-(heterocycyl)cycloalkyl]benzotriazoles 2, 5, and 8 or 1-[1-(heterocycyl)cyclohexyl]-5-phenyltetrazole (12 and 14). Intermediates 2, 5, 8, 12 and 14 were obtained by cyclizations of dihaloalkanes with N-(benzotriazol-1-ylmethyl)heterocycles, 1-imidazol-1-ylmethyl-5-phenyltetrazole (11), or 1-pyrazol-1-ylmethyl-5-phenyltetrazole (13) in the presence of n-BuLi.
ISSN:	0022-3263 1520-6904
DOI:	10.1021/jo020336m