Substituierte 3-Amino-thiophene und 3-Amino-selenophene aus ?-Chlor-?-cyan-zimts�urenitril

A novel synthesis of some new benzoyl‐substituted heterocycles from 2‐benzoyl‐3‐phenylpent‐2‐ene‐1,5‐dinitrile

“…The mixture was allowed to cool down, then poured on ice-cold water and acidified with HC1 till just neutral. The brown precipitate that appeared was collected by filtration and recrystallized from ethanol to afford (2 g, 68%) of 4, mp 232-233 °C; ir: max (KBr) 3430-3320 (NH 2 ), 2212 (CN), 1680 (C=O) cm -1 , (m/e=304); 1 was found to be identical with an authentic sample obtained from the reaction of 1 with elemental sulfur as described in the literature for similar systems [5]. Anal.…”

“…Compound 2a reacts with sodium hydrogen sulfide [5] in refluxing ethanol to afford a dark yellowish brown solid product. The IR spectrum of this product showed absorption bands at v 3430-3320 (NH 2 ), 2212 (CN) and F. M. Abdelrazek, S. A. Ghozlan, F. A. Michael Vol 44 1680 (CO) cm -1 respectively.…”

“…Experimental part). The formation of these products is assumed to proceed via the initial elimination of HBr to afford the acyclic intermediates 5, 7 and 9 respectively, followed by cyclization [5,7] to afford the final isolable products. This behaviour is similar to a previously reported work on related systems [8,9].…”

Bromonitromethane: A Versatile Reagent in Organic Synthesis

“…In another paper, thiophene c was synthesized by Gewald and Hain, starting from disubstituted b-chloroacrylonitrile, sodium sulfide and bromonitromethane. 7 The formation of 5-phenyl-3-amino-2-nitroselenophene (d) was also observed.…”

Synthesis of Selenophenes

“…Successive reactions of β-cinnamonitrile with sodium selenide, produced in situ with elemental selenium and sodium borohydride, and α-chloro-keto compounds have been used for the preparation of 5-substituted-4-amino-2phenylselenophene-3-carbonitrile [135].…”