ChemInform Abstract: Indolo(3,2‐d) (2,3)benzodiazepine Derivatives.

Abstract

ChemInform Abstract The title compounds (V), which represent a hitherto unknown ring system, can be prepared starting from the indoles (I) via the hydrazides (III). Structure (V) is also established by an alternative pathway starting from (III) via the ketones (VII). Some intermediates in the reactions (III) → (V) and (III) → (VII) are tested for their antibacterial activity. In some cases, moderate togood effects are observed.

Copper‐Catalyzed Synthesis of Indole‐Fused Benzodiazepines[1]

“…In our endeavors to develop novel pathways to annulated indoles, [4] we envisioned that our method could also be applied to 3-iodo-1H-indole-2-carbaldehydes for achieving the synthesis of indole-fused benzodiazepines. An isolated report [5] in the literature discloses the preparation of indoleA C H T U N G T R E N N U N G [3,2-b]A C H T U N G T R E N N U N G [1,5]benzodiazepine via an initial Cu 2 O-mediated Ullman reaction between 3-aminoindoles and 2-chloroaniline followed by acylation and subsequent cyclization with POCl 3 . This approach invariably produced C-6 substituted indole-A C H T U N G T R E N N U N G [3,2-b]A C H T U N G T R E N N U N G [1,5]benzodiazepines.…”

“…An isolated report [5] in the literature discloses the preparation of indoleA C H T U N G T R E N N U N G [3,2-b]A C H T U N G T R E N N U N G [1,5]benzodiazepine via an initial Cu 2 O-mediated Ullman reaction between 3-aminoindoles and 2-chloroaniline followed by acylation and subsequent cyclization with POCl 3 . This approach invariably produced C-6 substituted indole-A C H T U N G T R E N N U N G [3,2-b]A C H T U N G T R E N N U N G [1,5]benzodiazepines. We wish to provide an update on the use of our methodology for successfully preparing the indole-fused benzodiazepine.…”

Synthesis, spectral characterization and biological activity studies of transition metal complexes of Schiff base ligand containing indole moiety

“…Solvents were dried and distilled before use according to standard methods [10]. The precursor 3,5-dimethylindole-2-carbohydrazide was prepared by standard method [11]. The metal chlorides were used in their hydrated form.…”

Chemistry and heterocyclization of carbohydrazides

“…Carbohydrazides 1 underwent condensation with ethyl chloroformate to give N ‐carbethoxy‐5‐substituted indole‐2‐carbohydrazides 155 , which were refluxed in diethyl ether to give 2‐(5′‐oxo‐1′,3′,4′‐oxadiazol‐2′‐yl)indole derivatives 156 [104]. …”

“…Also, 1 was refluxed with appropriate quantities of KOH and CS 2 in ethanol to give oxadiazolethione derivatives 157 [104].…”