Synthesis of α-CF 3 - and α-CCl 3 substituted nitrogen heterocycles by aza Diels-Alder and cyclocondensation reactions

Diels–Alder Reaction in the Synthesis of Fluorinated (Hetero)Aromatic Compounds

“…Synthesis of pyridazine 339 by reaction of intermediate diaza‐diene 318 with CF 3 ‐containing enamine 337 …”

“…Recently Onys'ko et al published the first examples of [4+2]‐cycloaddition of several N‐activated imidoyl chlorides as aza‐dienophiles , . with dienes.…”

“…with dienes. Among others, N ‐(chlorosulfonyl)trifluoroacetimidoyl chloride ( 340 ) was used for the synthesis of pyridine 342 through intermediate 341 (Scheme ) . Similar chemistry was carried out also with N ‐phosphoryltrifluoroacetimidoyl chloride…”

Enantiomeric N‐tert‐Butylsulfinyl Imines of Methyl Trifluoropyruvate: Promising Building Blocks in Asymmetric Synthesis of α‐Trifluoromethylated Amino Acids and Derivatives

“…α‐Methyl substituted push‐pull enamines are known to react with electrophilic compounds with an involvement of nitrogen atom, β‐ or β′‐position of enamine, the reaction route depends on the structure of both imine and enamine [10] . Specifically, primary and secondary enamines 12 a and 12 b have shown opposite regioselectivity in cyclocondensation with N‐chlorosulfonyltrichloroacetimidoyl chloride [10d] . Reactions of sulfinyl imines with push‐pull enamines were not studied so far.…”

Fluorinated NH-iminophosphonates in synthesis of biorelevant α-aminophosphonic acids derivatives

“…Compounds of such type are known to reveal a wide spectrum of biological activity. α-Methyl-substituted push-pull enamines are other types of polyfunctional nucleophilic agents that are known to react with the involvement of nitrogen atom, βor β′-position of enamine [16][17][18]. In particular, reactions with imines can lead to completely different products depending on the substituents at the C=N bond.…”