tert-Butoxy Bis(dimethyl-amino)methane (Bredereck’s Reagent)

Abstract

This feature focuses on a reagent chosen by a postgraduate, highlighting the uses and preparation of the reagent in current research tert-Butoxy Bis(dimethylamino)methane (Bredereck's Reagent)Compiled by Giovanni Bernardi Rosso Giovanni B. Rosso was born in Uruguaiana, RS (South of Brazil) in 1973. Giovanni received his B.Sc. from Universidade Federal de Santa Maria (Santa Maria, RS) in 1998. His masters degree was carried out in the same institution (1998)(1999)(2000) under the supervision of Professor Mara E. F. Braibante, exploring the reactivity of b-enamino compounds under solid support (Montmorillonite/K-10). In 2000, he moved to Campinas, SP to work at Universidade Estadual de Campinas (UNICAMP) under supervision of Professor Ronaldo A. Pilli. His Ph.D. work concerns studies toward the synthesis and structural elucidation of Stemona alkaloid Parvistemoamide by a Michael addition reaction sequence. He has had a long-standing interest in the total synthesis of natural products, especially those of marine flora and fauna.

Discovery of Riociguat (BAY 63‐2521): A Potent, Oral Stimulator of Soluble Guanylate Cyclase for the Treatment of Pulmonary Hypertension

“…In a more convenient approach we used enamines 37 d-i as reactants in the cyclocondensation, as these are readily accessible using Bredereck's reagent [23] (Scheme 6). During optimization of the heterocyclization step we found that prolonged heating in xylene resulted in only trace amounts of the aminopyrimidines (compounds 18 and 22).…”

Synthesis, Characterization, and Pharmacological Evaluation of Some New Pteridine‐Based Heterocycles as Antimicrobial Agents

“…HCl acid, which afforded a single product [monitored by thin-layer chromatography (TLC)]. The elemental and spectral data of the isolated products were compatible with those of benzo[g] [1,3,5] thiadiazino [2,3-b] (15)(16)(17)(18)(19)(20)(21)(22)(23)(24), is shown in Scheme 4.…”

“…Previously reported works [37][38][39][40][41] have shown that the cyclization of S-alkylated pyrimidinone intermediates 14 occurs at the amidic N-atom, rather than the other Natom, based on 13 C NMR data. For instance, the 13 C NMR spectrum of compound 19 declared carbonyl carbon signal of the pyrimidinone at 162.9 ppm, indicating the N-atom adjacent to carbonyl is sp 3 hybridized, which is different from carbonyl adjacent to a sp 2 hybridized nitrogen that usually appears at 170-175 ppm [42]. Consequently, the structure of analogous 15-24 existed in one form, namely, A rather than B.…”

“…Natural compounds containing pteridines, such as erythropterin, xanthopterin, isoxanthopterin, lacticacid and leucopterin ( Fig. 1), play a significant role in growth processes, metabolism, biological coloration [2], and medicine as antiviral, anticancer, antibacterial, anddiuretic drugs [3]. Pteridines are heterocycles encompass a fused pyrimidine and pyrazine ring involved in a vast range of biological tasks from the color of butterfly wings to cofactors in enzyme catalysis to essential vitamins [4].…”

A New Synthesis of Pteridines Substituted with Branched and Linear Alkenyl Groups at C(6). The Nitroso‐Ene Reaction of 4‐(Alkenoylamino)‐5‐nitrosopyrimidines

“…As expected, the amidine 9 obtained by treating (E)-6 with Brederecks reagent [16] proved much more soluble in a range of apolar solvents than 6 [17]. Crystals of 9 suitable for X-ray analysis 4 ) were obtained by slowly concentrating a solution in MeCN.…”