vilsmeier-haack reaction with 2,3,3-trimethyl-3h-benzo[g]indole and its conversion into 2-(1-aryl-1h-pyrazol-4-yl)-3,3-dimethyl-3h-benzo[g]indoles

نویسندگان

mohsen khezri

department of organic chemistry, faculty of chemistry, university of urmia, urmia 57153-165, iran arash afghan

urmia university of technology, urmia, iran laya roohi

department of organic chemistry, faculty of chemistry, university of urmia, urmia 57153-165, iran mohammad mehdi baradarani

department of organic chemistry, faculty of chemistry, university of urmia, urmia 57153-165, iran

چکیده

vilsmeier-haack reaction of 2,3,3-trimethyl-3h-benzo[g]indole, then aqueous basic work-up, leads to benzo[g]indol-2-ylidene- malondialdehydes. these react with various arylhydrazines and quinolin-2-ylhydrazine to form 3,3-dimethyl-2-(1-aryl-1h-pyrazol-4-yl)- 3h-benzo[g]indoles in good yields.

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منابع مشابه

Vilsmeier-Haack Reaction with 2,3,3-Trimethyl-3H-benzo[g]indole and Its Conversion into 2-(1-aryl-1H-pyrazol-4-yl)-3,3-dimethyl-3H-benzo[g]indoles

Vilsmeier-Haack reaction of 2,3,3-trimethyl-3H-benzo[g]indole, then aqueous basic work-up, leads to benzo[g]indol-2-ylidene- malondialdehydes. These react with various arylhydrazines and quinolin-2-ylhydrazine to form 3,3-dimethyl-2-(1-aryl-1H-pyrazol-4-yl)- 3H-benzo[g]indoles in good yields.

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7-Chloro-2-[1-(4-methoxy­phen­yl)pyrazol-4-yl]-3,3-dimethyl-3H-indole

In the title compound, C(20)H(18)ClN(3)O, the dihedral angle between the pyrazole and the 3H-indole components is only 13.28 (6)°, indicating that there is conjugation between the two heterocyclic subunits. The N-methoxy-phenyl unit makes a dihedral angle of 25.10 (7)° with the pyrazole ring.

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In the title compound, C18H15N3O2, the benzo-furan ring system is essentially planar, the rings making a dihedral angle of 0.57 (9)°. The phenyl, furan and benzene rings subtend dihedral angles of 47.07 (10), 85.76 (7) and 86.04 (7)°, respectively, with the pyrazole ring. In the crystal, mol-ecules are linked by weak N-H⋯N, N-H⋯O and C-H⋯O inter-actions, generating edge-fused R 4 (4)(20), and R...

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In the crystal of the title salt, C(26)H(34)N(2) (2+)·2I(-), the dication lies on a center of inversion that exists along the mid-point of the butyl chain; its five-membered ring is approximately planar (r.m.s. deviation = 0.011 Å). In the crystal, the iodide anion is disordered over two positions in a 1:1 ratio.

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(3,5-Dimethyl-1H-pyrazol-1-yl){3-[(3,5-dimethyl-1H-pyrazol-1-yl)carbon­yl]-5-methyl­indolizin-1-yl}methanone

There are two independent mol-ecules in the asymmetric unit of the title compound, C21H21N5O2. In each mol-ecule, the indolizine ring system is essentially planar, with r.m.s. deviations of 0.030 and 0.028 Å. The dihedral angles between the indolizine ring system and the pyrazole rings are 54.7 (3) and 8.6 (3)° in one mol-ecule and 54.4 (3) and 6.6 (3)° in the other. In the crystal, weak C-H⋯O ...

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4-(3,5-Dimethyl-1H-pyrazol-1-yl)benzene­sulfonamide

The two aromatic rings of the title compound, C(11)H(13)N(3)O(2)S, are inclined at an angle of 47.81 (4)°. The N atom of the amino unit is pyramidally coordinated; one H atom inter-acts with the sulfamyl O atom of an adjacent mol-ecule, forming a centrosymmetric hydrogen-bonded dimer. The dimers are linked by N-H⋯N hydrogen bonds, generating a three-dimensional network.

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عنوان ژورنال:
organic chemistry research

جلد ۲، شماره ۲، صفحات ۱۲۰-۱۲۶

کلمات کلیدی
[ ' v i l s m e i e r ' , ' h a a c k r e a c t i o n ' , ' f o r m y l a t i o n ' , ' p y r a z o l e ' , ' m a l o n d i a l d e h y d e ' , 2 , ' q u i n o l y l h y d r a z i n e ' , ' a r y l h y d r a z i n e ' ]

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