Convenient Methodology for the Synthesis of Trialkylhydrazines

ALVARO J. VÁZQUEZ; CRISTIAN RODRIGUEZ; NORMA SBARBATI NUDELMAN

SYNTHETIC COMMUNICATIONS

TAYLOR & FRANCIS INC

Lugar: Filadelfia; Año: 2009 vol. 39 p. 3958 - 3972

0039-7911

A convenient methodology, based on the addition of organolithium compounds to N-nitrosamines, was developed for the synthesis of Substituted hydrazones and trialkyl hydrazines. The reaction is very sensitive to the reaction conditions, particularly the [RLi]?nitrosamine] ratio. For molar ratios of 1-1.2,an almost quantitative conversion to the NO bond addition products (i.e.,alkylhydrazones) can be obtained in very good yields, with any remaining nitro-samine. Using greater molar ratios (in the range of 3?5), a second addition occurs,and branched trialkyl hydrazines are obtained, in good yields, with variable amounts of hydrazone remaining. Substituted hydrazines are known to have useful commercial applications and remarkable biological activities. A wide diversity of trialkyl hydrazines could be synthesized by using two different organolithiums.