Synthesis, Spectroscopic and Crystal Structure Analysis of 2-amino-5,5-dimethyl-7-oxo-4,5,6,7-tetrahydro-1-benzothiophene-3-carbonitrile and -3-carboxamide

Begum, Noor Shahina; Vasundhara, D. E.; Lamani, Ravi S.; Hegde, Vinayak; Khazi, I. M.

doi:10.3184/030823409x425073

Cited by 3 publications

(1 citation statement)

References 13 publications

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“…Therefore, the overall yield of the reaction was cut down. Taking all these factors into account, the synthesis of compounds 1 was divided into two parts with shorter time and higher yield when TEA and diethylamine were used as catalysts in different steps (Scheme ) .…”

Section: Resultsmentioning

confidence: 99%

Convenient and Efficient Synthesis of 11-Amino-2,8-substituted-2,3,8,9-tetrahydrobenzo[4,5]thieno[2,3-b]quinolinone Derivatives

Wang

Chen

et al. 2014

J. Heterocyclic Chem.

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The Gewald reactions of 5‐substituted‐1,3‐cyclohexanedione, malononitrile, and powdered sulfur were carried out to give the corresponding products 2‐amino‐5‐substituted‐7‐oxo‐4,5,6,7‐tetrahydrobenzo[b]thiophene‐3‐carbonitrile derivatives 1. The intermediate enamines 2 were prepared by reaction of compounds 1 and 5‐substituted‐1,3‐cyclohexanedione with hydrochloric acid as catalyst. The title compounds 11‐amino‐2,8‐substituted‐2,3,8,9‐tetrahydrobenzo[4,5]thieno[2,3‐b]quinolinone 3 were synthesized by cyclization of compounds 2 in the presence of K2CO3 and Cu2Cl2. The structures of all compounds were characterized by elemental analysis, IR, MS, and 1H‐NMR spectra.

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Section: Resultsmentioning

confidence: 99%

Convenient and Efficient Synthesis of 11-Amino-2,8-substituted-2,3,8,9-tetrahydrobenzo[4,5]thieno[2,3-b]quinolinone Derivatives

Wang

Chen

et al. 2014

J. Heterocyclic Chem.

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ChemInform Abstract: Synthesis, Spectroscopic and Crystal Structure Analysis of 2‐Amino‐5,5‐dimethyl‐7‐oxo‐4,5,6,7‐tetrahydro‐1‐benzothiophene‐3‐carboni trile and ‐3‐carboxamide.

et al. 2009

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The Gewald reaction in dye chemistry

Sabnis¹

2016

Coloration Technology

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This review presents the most elegant and promising set of synthetic routes for the synthesis of 2‐aminothiophenes by the Gewald reaction. This reaction has applications in several applied fields, such as pharmaceuticals/biomedicine, agrochemicals, carbohydrate conjugates, sugar cane ripeners, peptide analogues, dyestuffs, and electronic materials; however, the present review will focus on the use of Gewald chemistry in the synthesis of conventional and functional colourants. The Gewald reaction produces 2‐aminothiophene, which is a key intermediate for the diazotisation reaction and for the synthesis of azo dyes, and thus opened the door for new dye chemistry. The reaction produces electron‐withdrawing groups such as CN, COOEt, COOMe, CONH2, and COPh in the 3‐ and/or 5‐position, resulting in bathochromic shifts for the deeper colours of the dyes. The review further reveals the importance of this reaction in the synthesis of azo dyes, fluorescent dyes (coumarin dyes, styryl dyes, thieno[2,3‐d]pyrimidine dyes, bithiophene dyes), thiophene analogues of phthalocyanines, and fluorescent whitening agents.

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Synthesis, Spectroscopic and Crystal Structure Analysis of 2-amino-5,5-dimethyl-7-oxo-4,5,6,7-tetrahydro-1-benzothiophene-3-carbonitrile and -3-carboxamide

Abstract: The preparation of 2-amino-5,5-dimethyl-7-oxo-4,5,6,7-tetrahydro-1-benzothiophene-3-carboxamide via the intermediate 2-amino-5,5-dimethyl-7-oxo-4,5,6,7-tetrahydro-1-benzothiophene-3-carbonitrile is described, along with details ofthe crystal structure analysis of both compounds.

Cited by 3 publications

References 13 publications

Convenient and Efficient Synthesis of 11-Amino-2,8-substituted-2,3,8,9-tetrahydrobenzo[4,5]thieno[2,3-b]quinolinone Derivatives

Convenient and Efficient Synthesis of 11-Amino-2,8-substituted-2,3,8,9-tetrahydrobenzo[4,5]thieno[2,3-b]quinolinone Derivatives

ChemInform Abstract: Synthesis, Spectroscopic and Crystal Structure Analysis of 2‐Amino‐5,5‐dimethyl‐7‐oxo‐4,5,6,7‐tetrahydro‐1‐benzothiophene‐3‐carboni trile and ‐3‐carboxamide.

The Gewald reaction in dye chemistry

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