Preparation of N ‐Aminoaziridines: trans ‐1‐Amino‐2,3‐Diphenylaziridine, 1‐Amino‐2‐Phenylaziridine, and 1‐Amino‐2‐Phenylaziridinium Acetate

Abstract

Preparation of N ‐aminoaziridines: trans ‐1‐amino‐2,3‐diphenylaziridine, 1‐amino‐2‐phenylaziridine, and 1‐amino‐2‐phenylaziridinium acetate intermediate: trans‐2,3‐ Diphenyl ‐1‐ phthalimidoaziridine product: trans‐1‐ Amino ‐2,3‐ diphenylaziridine product: Styrene glycol dimesylate product: 1‐amino‐2‐phenylaziridine product: 1‐amino‐2‐phenylaziridinium acetate

The Use of Tosylhydrazone Salts as a Safe Alternative for Handling Diazo Compounds and Their Applications in Organic Synthesis

“…It is noteworthy that other alternatives such as the use of phenyliodonium ylides, N ‐aziridinylimines and amino ester hydrochloride derived diazo compounds have been developed, although they will not be discussed in this article. The use of phenyliodonium ylides hasrecently been reviewed by Müller,29 N ‐aziridinylimines cannot be regarded as safer than diazo compounds due to the explosive nature of its precursor, 1‐amino‐2‐phenyl‐aziridinium acetate 30,31. Amino ester hydrochlorides have found limited use as they are only used to generate diazoacetates by diazotization 32,33.…”

Tranylcypromine‐Based LSD1 Inhibitors: Structure‐Activity Relationships, Antiproliferative Effects in Leukemia, and Gene Target Modulation

“…Afterward, we applied some chemical modifications to the TCP structure by preparing compounds 4 a – h , in which the primary amine group of TCP has been changed into secondary ( N ‐methyl‐TCP, 4 a ) or tertiary ( N , N ‐dimethyl‐TCP, 4 b ) amine, or transformed into carboxamide ( 4 c ) or carbohydrazide ( 4 d ). The isomeric 1‐phenylcyclopropan‐1‐amine ( 4 e ) and the related benzyl {1‐[(4‐(1‐aminocyclopropyl)phenyl)amino]‐1‐oxo‐3‐phenylpropan‐2‐yl}carbamate hydrochloride ( 4 f , a 2 a isomer) were also prepared, together with the related 1‐phenylcyclopropane‐1‐carboxamide ( 4 g ), (1‐phenylcyclopropyl)methanamine ( 4 h ), and 2‐phenylaziridin‐1‐amine ( 4 i ) . Compounds 4 a , b , h , i were prepared according to the reported procedures, while 4 c , d were obtained by treating the commercially available 2‐phenylcyclopropane‐1‐carboxylic acid with PyBOP, 33 % ammonia and triethylamine (for 4 c ), or its methyl ester with hydrazine hydrate (for 4 d ) (Scheme A).…”

Diastereotopic group selectivity and chemoselectivity of alkylidene carbene reactions on 8-oxabicyclo[3.2.1]oct-6-ene ring systems

“…Vanadium-catalysed epoxidation allowed for selective oxidation of the exocyclic alkene in 11a. 18 Protection of the tertiary alcohol as a TMS ether 14 followed by condensation with the hydrazine derived from ammonium salt 15 19 gave the target N-aziridinylimine 16. The presence of a primary alcohol is also important to achieve the desired chemoselectivitythe corresponding TBS ether of 11a (containing a tertiary alcohol) failed to undergo vanadium-catalysed epoxidation at either alkene.…”