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Expedient approach for the synthesis of novel indenothiophene derivatives
Gewald reaction of 2-(2,3-dihydro-5,6-dimethoxy-1 H -inden-1-ylidene)malononitrile, elemental sulfur, and a catalytic amount of triethylamine furnished the new synthon 2-aminoindenothiophene-3-carbonitrile. Its reaction with conc. H 2 SO 4 furnished the expected 2-amino-3-carboxamide derivative inst...
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| Published in: | Monatshefte für Chemie 2012-02, Vol.143 (2), p.317-323 |
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| Main Authors: | , , , , , |
| Format: | Article |
| Language: | English |
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| cited_by | cdi_FETCH-LOGICAL-c288t-c3db3d60c7f6c7afc10269bfbe01ea620d5f24dbceaa66cad2d6a4e69b1a425f3 |
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| cites | cdi_FETCH-LOGICAL-c288t-c3db3d60c7f6c7afc10269bfbe01ea620d5f24dbceaa66cad2d6a4e69b1a425f3 |
| container_end_page | 323 |
| container_issue | 2 |
| container_start_page | 317 |
| container_title | Monatshefte für Chemie |
| container_volume | 143 |
| creator | Patil, Shivaraj P. Kazi, Muddassar A. Kanawade, Shrikant B. Nikam, Prashant S. Jachak, Madhukar N. Toche, Raghunath B. |
| description | Gewald reaction of 2-(2,3-dihydro-5,6-dimethoxy-1
H
-inden-1-ylidene)malononitrile, elemental sulfur, and a catalytic amount of triethylamine furnished the new synthon 2-aminoindenothiophene-3-carbonitrile. Its reaction with conc. H
2
SO
4
furnished the expected 2-amino-3-carboxamide derivative instead of the corresponding carboxylic acid. The key intermediates 2-aminoindenothiophene-3-carbonitrile and -3-carboxamide were used for the synthesis of tetracyclic indenothienopyrimidine derivatives by cyclocondensation reaction with acid chlorides, amides, formic acid, or hydrazine hydrate. Neat reactions of the carbonitrile with cyclic and aliphatic ketones in the presence of anhydrous ZnCl
2
furnished pentacyclic and tetracyclic indenothienopyridine derivatives, respectively, in good yields. All new compounds were characterized by spectroscopic and analytical data.
Graphical abstract |
| doi_str_mv | 10.1007/s00706-011-0657-5 |
| format | article |
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H
-inden-1-ylidene)malononitrile, elemental sulfur, and a catalytic amount of triethylamine furnished the new synthon 2-aminoindenothiophene-3-carbonitrile. Its reaction with conc. H
2
SO
4
furnished the expected 2-amino-3-carboxamide derivative instead of the corresponding carboxylic acid. The key intermediates 2-aminoindenothiophene-3-carbonitrile and -3-carboxamide were used for the synthesis of tetracyclic indenothienopyrimidine derivatives by cyclocondensation reaction with acid chlorides, amides, formic acid, or hydrazine hydrate. Neat reactions of the carbonitrile with cyclic and aliphatic ketones in the presence of anhydrous ZnCl
2
furnished pentacyclic and tetracyclic indenothienopyridine derivatives, respectively, in good yields. All new compounds were characterized by spectroscopic and analytical data.
Graphical abstract</description><identifier>ISSN: 0026-9247</identifier><identifier>EISSN: 1434-4475</identifier><identifier>DOI: 10.1007/s00706-011-0657-5</identifier><language>eng</language><publisher>Vienna: Springer Vienna</publisher><subject>Analytical Chemistry ; Chemistry ; Chemistry and Materials Science ; Chemistry/Food Science ; Inorganic Chemistry ; Organic Chemistry ; Original Paper ; Physical Chemistry ; Theoretical and Computational Chemistry</subject><ispartof>Monatshefte für Chemie, 2012-02, Vol.143 (2), p.317-323</ispartof><rights>Springer-Verlag 2011</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c288t-c3db3d60c7f6c7afc10269bfbe01ea620d5f24dbceaa66cad2d6a4e69b1a425f3</citedby><cites>FETCH-LOGICAL-c288t-c3db3d60c7f6c7afc10269bfbe01ea620d5f24dbceaa66cad2d6a4e69b1a425f3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27923,27924</link.rule.ids></links><search><creatorcontrib>Patil, Shivaraj P.</creatorcontrib><creatorcontrib>Kazi, Muddassar A.</creatorcontrib><creatorcontrib>Kanawade, Shrikant B.</creatorcontrib><creatorcontrib>Nikam, Prashant S.</creatorcontrib><creatorcontrib>Jachak, Madhukar N.</creatorcontrib><creatorcontrib>Toche, Raghunath B.</creatorcontrib><title>Expedient approach for the synthesis of novel indenothiophene derivatives</title><title>Monatshefte für Chemie</title><addtitle>Monatsh Chem</addtitle><description>Gewald reaction of 2-(2,3-dihydro-5,6-dimethoxy-1
H
-inden-1-ylidene)malononitrile, elemental sulfur, and a catalytic amount of triethylamine furnished the new synthon 2-aminoindenothiophene-3-carbonitrile. Its reaction with conc. H
2
SO
4
furnished the expected 2-amino-3-carboxamide derivative instead of the corresponding carboxylic acid. The key intermediates 2-aminoindenothiophene-3-carbonitrile and -3-carboxamide were used for the synthesis of tetracyclic indenothienopyrimidine derivatives by cyclocondensation reaction with acid chlorides, amides, formic acid, or hydrazine hydrate. Neat reactions of the carbonitrile with cyclic and aliphatic ketones in the presence of anhydrous ZnCl
2
furnished pentacyclic and tetracyclic indenothienopyridine derivatives, respectively, in good yields. All new compounds were characterized by spectroscopic and analytical data.
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H
-inden-1-ylidene)malononitrile, elemental sulfur, and a catalytic amount of triethylamine furnished the new synthon 2-aminoindenothiophene-3-carbonitrile. Its reaction with conc. H
2
SO
4
furnished the expected 2-amino-3-carboxamide derivative instead of the corresponding carboxylic acid. The key intermediates 2-aminoindenothiophene-3-carbonitrile and -3-carboxamide were used for the synthesis of tetracyclic indenothienopyrimidine derivatives by cyclocondensation reaction with acid chlorides, amides, formic acid, or hydrazine hydrate. Neat reactions of the carbonitrile with cyclic and aliphatic ketones in the presence of anhydrous ZnCl
2
furnished pentacyclic and tetracyclic indenothienopyridine derivatives, respectively, in good yields. All new compounds were characterized by spectroscopic and analytical data.
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| subjects | Analytical Chemistry Chemistry Chemistry and Materials Science Chemistry/Food Science Inorganic Chemistry Organic Chemistry Original Paper Physical Chemistry Theoretical and Computational Chemistry |
| title | Expedient approach for the synthesis of novel indenothiophene derivatives |
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