A metal free reduction of aryl-N-nitrosamines to the corresponding hydrazines using a sustainable reductant thiourea dioxide

• Published in: Green chemistry : an international journal and green chemistry resource : GC Vol. 18; no. 23; pp. 6215 - 6221
• Main Authors: Chaudhary, Priyanka, Gupta, Surabhi, Sureshbabu, Popuri, Sabiah, Shahulhameed, Kandasamy, Jeyakumar
• Format: Journal Article
• Language: English
• Published: CAMBRIDGE Royal Soc Chemistry 01.01.2016
• Subjects: Alkynes; Chemistry; Chemistry, Multidisciplinary; Dioxides; Green & Sustainable Science & Technology; Hydrazines; Olefins; Physical Sciences; Reduction (metal working); Science & Technology; Science & Technology - Other Topics; Sustainability; Synthesis; Thioureas; ONE-POT SYNTHESIS; FISCHER INDOLIZATION; ANALOGS; ALKYLATION; N,N-DISUBSTITUTED HYDRAZINES; EFFICIENT SYNTHESIS; BIOLOGICAL-ACTIVITIES; PHENYLHYDRAZINE; ANTAGONISTS; ARYLBORONIC ACIDS
• ISSN: 1463-9262; 1463-9270
• DOI: 10.1039/c6gc02444k

Reduction of aryl-N-nitrosamines to the corresponding hydrazines is reported under metal free conditions using a sustainable industrial reductant thiourea dioxide (TDO). The reaction takes place under mild conditions in an aqueous medium to provide good to excellent yields of the desired products. Sensitive functional groups such as olefins, alkynes and aryl halides were found to be stable during the reduction while a wide range of aryl-N-nitrosamines were successfully converted to the desired hydrazines. Onepot synthesis of arylhydrazines from their corresponding secondary amines via an N-nitrosamine intermediate was established.