A Simple Synthesis of 1-Acyl-3-aryl-3H-pyrrolo[2′,3′:4,5]pyrimido[6,1-b]benzothiazol-6-ium-2-olates: Betainic Derivatives of a Novel Heterocyclic System

Elizaveta V. Resnyanskaya; Anton V. Tverdokhlebov; Yulian M. Volovenko; Oleg V. Shishkin; Roman I. Zubatyuk

doi:10.1055/s-2002-35992

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A Simple Synthesis of 1-Acyl-3-aryl-3H-pyrrolo[2′,3′:4,5]pyrimido[6,1-b]benzothiazol-6-ium-2-olates: Betainic Derivatives of a Novel Heterocyclic System

Elizaveta V. Resnyanskaya^a, Anton V. Tverdokhlebov*^a, Yulian M. Volovenko^a, Oleg V. Shishkin^b, Roman I. Zubatyuk^b
^a Kiev National Taras Shevchenko University, Volodimirska str., 62, 01033, Kiev, Ukraine
e-Mail: atver@mail.univ.kiev.ua;
^b Scientific Research Department of Alkali Halide Crystals, STC ‘Institute for Single Crystals’, National Academy of Sciences of Ukraine, 60 Lenina ave., 310001, Khar’kov, Ukraine

Abstract

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Abstract

The title compounds were obtained by acylation of 5-amino-1-aryl-4-(2-benzothiazolyl)-2,3-dihydro-2-pyrrolones with 3-fold excess of acid chlorides. Starting pyrrolones were prepared in high yields by alkylation of 2-benzothiazoleacetonitrile with chloroacetic acid anilides. An X-ray crystallographic study of 1-benzoyl-3,5-diphenyl-3H-pyrrolo[2′,3′:4,5]pyrimido[6,1-b]benzothiazole-6-ium-2-olate was carried out to confirm the structure of title compounds unambiguously. The charge distribution in the obtained betaines was discussed.

Key words

acylations - alkylations - 5-amino-2-pyrrolones - heterocycles - pyrrolo[2′,3′:4,5]pyrimido[6,1-b]benzothiazoles

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