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Molecules ; 24(4)2019 Feb 15.
Artigo em Inglês | MEDLINE | ID: mdl-30769955


A novel banana-shaped molecule using 2,8-Dimethyl-6H,12H-5,11-methanodibenzo [b,f] [1,5]diazocine (Tröger's base) as bent-core was synthesized via double Carbon-Carbon cross-coupling reaction. The double Sonogashira cross-coupling reaction was optimized by using Pd(PPh3)2Cl2 as catalyst, CuI as cocatalyst and diisopropylamine as base in place of triethylamine. The structure of this compound was confirmed by ¹H-NMR, 13C-NMR, Fourier transform infrared (FT-IR) spectroscopy and mass spectrometry.

Técnicas de Química Sintética , Modelos Químicos , Estrutura Molecular , Compostos Orgânicos/química , Compostos Orgânicos/síntese química
Org Lett ; 20(11): 3332-3336, 2018 06 01.
Artigo em Inglês | MEDLINE | ID: mdl-29771129


A series of bibenzo[ b][1,4]thiazines with various functional groups has been synthesized by a free-radical condensation reaction. Bibenzo[ b][1,4]thiazines were obtained in moderate to good yield (up to 85%) through a one-step reaction of readily available 2,2'-dithiodianiline and methyl aryl ketones with AIBN as radical initiator in HOAc. Bibenzo[ b][1,4]thiazines exhibit diversiform solid-state packing.

J Org Chem ; 82(7): 3798-3805, 2017 04 07.
Artigo em Inglês | MEDLINE | ID: mdl-28299941


Two transition metal (Cu and Pd)-catalyzed C-S, C-N, and C-C bond cross-coupling reactions for the preparation of N-fused benzo[4,5]imidazo[2,1-b]thiazole derivatives were developed. A variety of 3-substituted and 2,3-disubstituted benzo[4,5]imidazo[2,1-b]thiazoles were efficiently and conveniently synthesized from the coupling reaction via trans-1,2-diiodoalkenes, 1H-benzo[d]imidazole-2-thiols, and halobenzenes in moderate to excellent yields.

J Org Chem ; 79(17): 8040-8, 2014 Sep 05.
Artigo em Inglês | MEDLINE | ID: mdl-25101862


A series of 1,4-thiazepin-5(4H)-one derivatives were synthesized via a transition metal-free one-pot Smiles rearrangement process at room temperature. Regioselective seven-membered heterocycles were constructed in good to excellent yields. To gain an in-depth understanding of the S-N type Smiles rearrangement mechanism, a theoretical study was also performed by quantum chemistry calculations.

Metais/química , Tiazepinas/síntese química , Elementos de Transição/química , Modelos Teóricos , Estrutura Molecular , Teoria Quântica , Estereoisomerismo , Tiazepinas/química
ACS Comb Sci ; 16(7): 328-32, 2014 Jul 14.
Artigo em Inglês | MEDLINE | ID: mdl-24919956


A one-pot transition metal-free method for synthesizing benzo[4,5]imidazo[1,2-a]quinazoline and imidazo[1,2-a]quinazoline derivatives has been developed. The approach is widely applicable to 2-fluoro-, 2-chloro-, 2-bromo- and 2-nitro-substituted aryl aldehyde and ketone substrates. The fluorescence properties of target compounds were studied.

Benzimidazóis/síntese química , Quinazolinas/síntese química , Aldeídos/química , Benzimidazóis/química , Cetonas/química , Estrutura Molecular , Quinazolinas/química
Org Biomol Chem ; 11(24): 4102-8, 2013 Jun 28.
Artigo em Inglês | MEDLINE | ID: mdl-23674063


A transition metal-free methodology for the synthesis of pyridazinopyrido[3,2-f][1,4]thiazepine-diones was studied. The construction of this tricyclic system went through a one-pot coupling/Smiles rearrangement/cyclization process. The high yields of pure products were obtained through simple recrystallization.

Compostos Heterocíclicos com 3 Anéis/síntese química , Piridazinas/síntese química , Tiazepinas/síntese química , Cristalografia por Raios X , Ciclização , Compostos Heterocíclicos com 3 Anéis/química , Modelos Moleculares , Estrutura Molecular , Piridazinas/química , Tiazepinas/química