Poster presentation
237
SYNTHESIS OF BENZO[4,5]IMIDAZO[2,1-B]QUINAZOLIN-
12(5H)-ONE
S.S. Saidov
1
, В.I. Avazova
2
, Sh.Kh. Kubaev
1
, R.Ya. Okmanov
1
1) S.Yu. Yunusov Institute of the Chemistry of Plant Substances Academy of sciences of
the Republic of Uzbekistan st. Mirzo-Ulugbek, 77, 100170 Tashkent
e-mail: sarvar-saidov-1989@bk.ru
2) Urgench State University. Kh. Alimdjan str., 14, Urgench city, 220100,
Uzbekistan
Benzimidazoles are heterocyclic aromatic organic
compound which have been an
important pharmacophore and privileged structure in medicinal chemistry. Many
substituted benzimidazoles have considerable interest as compounds with a wide
spectrum of biological activity and low toxicity.
Recently we have studied the interaction of 2-methoxycarbonylaminobenzimidazole
with benzoic and various aliphatic
carboxylic acids of
normal
or
iso
-structure. In this
case, the formation of mainly the corresponding acid amides was found [1].
Continuing
similar studies, in this work we curried out interaction of 2-
methoxycarbonylaminobenzimidazole (
2
) with 2-hydroxybenzoic acid (salicylic acid,
1
)
boiling in DMF of equimolar amounts of starting materials,
and formation of a new
annulated product – benzimidazo-quinazolinone (
3
) was observed (Scheme 1):
Scheme 1. Synthesis of benzo[4,5]imidazo[2,1-
b
]quinazolin-12(5
H
)-one
Based on the product (
3
) obtained, it can be assumed that during the reaction, takes
place regioselectively interaction of exocyclic amino group of the pre-formed 2-
aminobenzimidazole and carboxylic group of benzoic acid (
1
) to form benzoic acid
amide; then intramolecular cyclization of this intermediate (amide)
in acidic medium
occurs with the formation of the target annelated heterocyclic product (
3
).
For reliable refinement of the structure, X-ray structural analysis was performed:
Figure 1. Molecular structure of benzo[4,5]imidazo[2,1-
b
]quinazolin-12(5
H
)-one,
including atom labelling. Displacement ellipsoids are draw at the 30% probability level.
Reference
1. A.Sh. Abdurazakov, S.S. Saidov, R.Ya. Okmanov, Sh.Kh. Kubaev, B.Zh.
Elmuradov.
Egypt. J. Chem.
2021, Vol. 64, No. 5. P.2247-2252.
C1
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