N- and N′-aryl substitution in benzamidines

Abstract

N-Phenyl substitution of amino-and imino-groups in benzamidines is shown to reduce basic strength by factors of ca. 10 and 1000, respectively. The configuration of the imino-N-phenyl ring is discussed. The structure of the predominant tautomer of N -( 3-diethylaminopropyl)-N'-phenylbenzamidine is indicated.

Vallesiachotamine and Isovallesiachotamine from the Seeds of Strychnos tricalysioides

“…Vallesiachotamine and isovallesiachotamine can be formed by mild hydrolysis [3] or by the action of 3-glucosidase [7] on the tetrahydro-3-carboline monoterpenoid alkaloid strictosidine (V), also found in Rhazya species [8]. It seems probable that they are derived in the same way in S. tricalysioides but, so far, we have not been able to detect the presence of the putative precursor.…”

Understanding the Reactivity of Acyl Anion Equivalents: The Epoxide Ring Opening Case

“…[16] However, subsequent coupling of the substituted dithiane 11 (Scheme 2) with an epoxide, aldehyde or alkyl halide can be problematic, as first reported by Corey and Seebach, and later by others (Scheme 2).…”

The reaction of 2-amino- N ′-arylbenzamidines with tetracyanoethene reinvestigated: routes to imidazoles, quinazolines and quinolino[2′,3′:4,5]imidazo[1,2- c ]quinazoline-8-carbonitrile

“…prepared by reacting TCNE with (Z)-2-nitro-N'-phenylbenzamidine (25) to give (Z)-2-nitro-N'-phenyl-N-(1,2,2-tricyanovinyl)benzamidine (26) …”

“…2-Nitro-N'-pheny-N-(1,2,2-tricyanovinyl)benzamidine (26), CDCl 3 2-Nitro-N'-pheny-N-(1,2,2-tricyanovinyl)benzamidine (26), CDCl 3 , 13 …”