DOI: 10.1002/jhet.5570180407. Synthesis of 2‐aminochromones. Studies on the nucleophilic displacement of sulphinyl and sulphonyl groups in the 2‐position of 5,8‐dimethoxychromone

Synthesis of 2‐aminochromones. Studies on the nucleophilic displacement of sulphinyl and sulphonyl groups in the 2‐position of 5,8‐dimethoxychromone

10.1002/jhet.5570180407

Crossref journal-article

Wiley

Journal of Heterocyclic Chemistry (311)

Abstract

AbstractThe synthesis is described of a number of N‐substituted 2‐amino‐5,8‐dimethoxychromones (1) by replacement of the sulphoxide group in 2‐ethylsulphinyl‐5,8‐dimethoxychromone (5a) with the appropriate amine. Analogous substitution of 2‐ethylsulphonyl‐5,8‐dimethoxychromone (5b) is also possible but limited by the instability of the sulphone. Replacement reactions of 5a involving oxygen, sulphur, and phosphorus nucleophiles are also described.

Bibliography

Bantick, J. R., & Suschitzky, J. L. (1981). Synthesis of 2âaminochromones. Studies on the nucleophilic displacement of sulphinyl and sulphonyl groups in the 2âposition of 5,8âdimethoxychromone. Journal of Heterocyclic Chemistry, 18(4), 679â684. Portico.

Authors 2

J. R. Bantick (first)
J. L. Suschitzky (additional)

References 36 Referenced 40

10.1002/9780470187012
10.1246/bcsj.35.1869
{'key': 'e_1_2_1_3_3', 'first-page': '874', 'volume': '96', 'author': 'Cecchi S.', 'year': '1966', 'journal-title': 'Gazz. Chim. Ital.'} / Gazz. Chim. Ital. by Cecchi S. (1966)
(c)R. E.BrownandD. M.Lustgarten U. S. Patent 3 932 466 (1976)
{'key': 'e_1_2_1_3_5', 'first-page': '2283', 'volume': '51', 'author': 'Jermanowska Z.', 'year': '1977', 'journal-title': 'Rocz. Chem.'} / Rocz. Chem. by Jermanowska Z. (1977)
10.1248/cpb.24.644
10.1002/ardp.19723050912
{'key': 'e_1_2_1_6_2', 'first-page': '143', 'volume': '2', 'author': 'Glozman S. M.', 'year': '1970', 'journal-title': 'Khim. Geterotsikl. Soedin.'} / Khim. Geterotsikl. Soedin. by Glozman S. M. (1970)
{'key': 'e_1_2_1_6_3', 'first-page': '114184h', 'volume': '77', 'year': '1972', 'journal-title': 'Chem. Abstr.'} / Chem. Abstr. (1972)
{'key': 'e_1_2_1_7_2', 'first-page': '171', 'volume': '2', 'author': 'Zagorevskii V. A.', 'year': '1970', 'journal-title': 'Khim. Geterotsikl. Soedin.'} / Khim. Geterotsikl. Soedin. by Zagorevskii V. A. (1970)
{'key': 'e_1_2_1_7_3', 'first-page': '87288m', 'volume': '77', 'year': '1972', 'journal-title': 'Chem. Abstr.'} / Chem. Abstr. (1972)
U.PetersonandH.Heitzer Ann. Chem. 1659(1976)
10.1021/jo01298a042
{'key': 'e_1_2_1_9_2', 'first-page': '269', 'volume': '101', 'author': 'Ermili A.', 'year': '1971', 'journal-title': 'Gazz. Chim. Itai'} / Gazz. Chim. Itai by Ermili A. (1971)
{'key': 'e_1_2_1_9_3', 'first-page': '713', 'volume': '32', 'author': 'Ermili A.', 'year': '1977', 'journal-title': 'Gazz. Chim. Itai'} / Gazz. Chim. Itai by Ermili A. (1977)
10.1002/jhet.5570120604
{'key': 'e_1_2_1_10_2', 'first-page': '2819', 'volume': '250', 'author': 'Levas M.', 'year': '1960', 'journal-title': 'C. R. Acad. Sci., Ser. C'} / C. R. Acad. Sci., Ser. C by Levas M. (1960)
10.1002/ardp.19723050911
{'key': 'e_1_2_1_12_2', 'first-page': '193', 'volume': '3', 'author': 'Le Corrc M.', 'year': '1968', 'journal-title': 'Ann. Chim. (Paris)'} / Ann. Chim. (Paris) by Le Corrc M. (1968)
G. P.EllisandI. L.Thomas J. Chem. Soc Perkin Trans. I 2570(1974). (10.1039/p19740002570)
10.1002/jhet.5570150416
{'key': 'e_1_2_1_15_2', 'volume-title': 'Advances in Heterocyclic Chemistry', 'author': 'Shepherd R. G.', 'year': '1965'} / Advances in Heterocyclic Chemistry by Shepherd R. G. (1965)
(b)G. B.BarlinandW. V.Brown J. Chem. Soc. C 2473(1967). (10.1039/j39670002473)
G. B.BarlinandW. V.Brown J. Chem. Soc. B 1435(1968) (10.1039/j29680001435)
10.1002/cber.19781110321
F. M.Dean D. B.Frankham NatiqHatamandA. W.Hill J. Chem. Soc. C 218(1971). (10.1039/j39710000218)
10.1016/S0040-4020(01)93857-8
The pKa of 1c was 2.9 as measured spectrophotometrically.
10.1248/yakushi1947.96.7_841 / Yakugaku Zasshi by Komiya T. (1976)
{'key': 'e_1_2_1_20_3', 'first-page': '89536a', 'volume': '86', 'year': '1977', 'journal-title': 'Chem. Abstr.'} / Chem. Abstr. (1977)
10.3987/R-1977-09-1581
(c)E. K.AdesoganandA. L.Okunade J. Chem. Soc. Chem. Commun. 152(1978). (10.1039/c39780000152)
See for example R. B.King J. C.CloydandP. N.Kapoor J. Chem. Soc. Perkin Trans. I 2226(1973).
{'key': 'e_1_2_1_22_2', 'first-page': '483', 'volume': '26', 'author': 'Cieslak J.', 'year': '1952', 'journal-title': 'Rocz. Chem.'} / Rocz. Chem. by Cieslak J. (1952)
10.1139/v78-292
10.1021/jo00807a028

Dates

Type	When
Created	16 years, 5 months ago (March 11, 2009, 8:47 p.m.)
Deposited	1 year, 9 months ago (Nov. 6, 2023, 10:25 a.m.)
Indexed	5 days, 18 hours ago (Aug. 23, 2025, 9:12 p.m.)
Issued	44 years, 2 months ago (June 1, 1981)
Published	44 years, 2 months ago (June 1, 1981)
Published Online	16 years, 5 months ago (March 11, 2009)
Published Print	44 years, 2 months ago (June 1, 1981)

Funders 0

None

BibTeX

@article{Bantick_1981, title={Synthesis of 2‐aminochromones. Studies on the nucleophilic displacement of sulphinyl and sulphonyl groups in the 2‐position of 5,8‐dimethoxychromone}, volume={18}, ISSN={1943-5193}, url={http://dx.doi.org/10.1002/jhet.5570180407}, DOI={10.1002/jhet.5570180407}, number={4}, journal={Journal of Heterocyclic Chemistry}, publisher={Wiley}, author={Bantick, J. R. and Suschitzky, J. L.}, year={1981}, month=jun, pages={679–684} }

JSON

{
  "indexed": {
    "date-parts": [
      [
        2025,
        8,
        24
      ]
    ],
    "date-time": "2025-08-24T01:12:54Z",
    "timestamp": 1755997974922
  },
  "reference-count": 36,
  "publisher": "Wiley",
  "issue": "4",
  "license": [
    {
      "start": {
        "date-parts": [
          [
            2009,
            3,
            11
          ]
        ],
        "date-time": "2009-03-11T00:00:00Z",
        "timestamp": 1236729600000
      },
      "content-version": "vor",
      "delay-in-days": 10145,
      "URL": "http://onlinelibrary.wiley.com/termsAndConditions#vor"
    }
  ],
  "content-domain": {
    "domain": [],
    "crossmark-restriction": false
  },
  "published-print": {
    "date-parts": [
      [
        1981,
        6
      ]
    ]
  },
  "abstract": "<jats:title>Abstract</jats:title><jats:p>The synthesis is described of a number of <jats:italic>N</jats:italic>\u2010substituted 2\u2010amino\u20105,8\u2010dimethoxychromones (<jats:bold>1</jats:bold>) by replacement of the sulphoxide group in 2\u2010ethylsulphinyl\u20105,8\u2010dimethoxychromone (<jats:bold>5a</jats:bold>) with the appropriate amine. Analogous substitution of 2\u2010ethylsulphonyl\u20105,8\u2010dimethoxychromone (<jats:bold>5b</jats:bold>) is also possible but limited by the instability of the sulphone. Replacement reactions of <jats:bold>5a</jats:bold> involving oxygen, sulphur, and phosphorus nucleophiles are also described.</jats:p>",
  "DOI": "10.1002/jhet.5570180407",
  "type": "journal-article",
  "created": {
    "date-parts": [
      [
        2009,
        3,
        12
      ]
    ],
    "date-time": "2009-03-12T00:47:51Z",
    "timestamp": 1236818871000
  },
  "page": "679-684",
  "source": "Crossref",
  "is-referenced-by-count": 40,
  "title": "Synthesis of 2\u2010aminochromones. Studies on the nucleophilic displacement of sulphinyl and sulphonyl groups in the 2\u2010position of 5,8\u2010dimethoxychromone",
  "prefix": "10.1002",
  "volume": "18",
  "author": [
    {
      "given": "J. R.",
      "family": "Bantick",
      "sequence": "first",
      "affiliation": []
    },
    {
      "given": "J. L.",
      "family": "Suschitzky",
      "sequence": "additional",
      "affiliation": []
    }
  ],
  "member": "311",
  "published-online": {
    "date-parts": [
      [
        2009,
        3,
        11
      ]
    ]
  },
  "reference": [
    {
      "key": "e_1_2_1_2_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1002/9780470187012"
    },
    {
      "key": "e_1_2_1_3_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1246/bcsj.35.1869"
    },
    {
      "key": "e_1_2_1_3_3",
      "first-page": "874",
      "volume": "96",
      "author": "Cecchi S.",
      "year": "1966",
      "journal-title": "Gazz. Chim. Ital."
    },
    {
      "key": "e_1_2_1_3_4",
      "unstructured": "(c)R. E.BrownandD. M.Lustgarten U. S. Patent 3 932 466 (1976)"
    },
    {
      "key": "e_1_2_1_3_5",
      "first-page": "2283",
      "volume": "51",
      "author": "Jermanowska Z.",
      "year": "1977",
      "journal-title": "Rocz. Chem."
    },
    {
      "key": "e_1_2_1_4_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1248/cpb.24.644"
    },
    {
      "key": "e_1_2_1_5_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1002/ardp.19723050912"
    },
    {
      "key": "e_1_2_1_6_2",
      "first-page": "143",
      "volume": "2",
      "author": "Glozman S. M.",
      "year": "1970",
      "journal-title": "Khim. Geterotsikl. Soedin."
    },
    {
      "key": "e_1_2_1_6_3",
      "first-page": "114184h",
      "volume": "77",
      "year": "1972",
      "journal-title": "Chem. Abstr."
    },
    {
      "key": "e_1_2_1_7_2",
      "first-page": "171",
      "volume": "2",
      "author": "Zagorevskii V. A.",
      "year": "1970",
      "journal-title": "Khim. Geterotsikl. Soedin."
    },
    {
      "key": "e_1_2_1_7_3",
      "first-page": "87288m",
      "volume": "77",
      "year": "1972",
      "journal-title": "Chem. Abstr."
    },
    {
      "key": "e_1_2_1_8_2",
      "unstructured": "U.PetersonandH.Heitzer Ann. Chem. 1659(1976)"
    },
    {
      "key": "e_1_2_1_8_3",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/jo01298a042"
    },
    {
      "key": "e_1_2_1_9_2",
      "first-page": "269",
      "volume": "101",
      "author": "Ermili A.",
      "year": "1971",
      "journal-title": "Gazz. Chim. Itai"
    },
    {
      "key": "e_1_2_1_9_3",
      "first-page": "713",
      "volume": "32",
      "author": "Ermili A.",
      "year": "1977",
      "journal-title": "Gazz. Chim. Itai"
    },
    {
      "key": "e_1_2_1_9_4",
      "doi-asserted-by": "publisher",
      "DOI": "10.1002/jhet.5570120604"
    },
    {
      "key": "e_1_2_1_10_2",
      "first-page": "2819",
      "volume": "250",
      "author": "Levas M.",
      "year": "1960",
      "journal-title": "C. R. Acad. Sci., Ser. C"
    },
    {
      "key": "e_1_2_1_11_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1002/ardp.19723050911"
    },
    {
      "key": "e_1_2_1_12_2",
      "first-page": "193",
      "volume": "3",
      "author": "Le Corrc M.",
      "year": "1968",
      "journal-title": "Ann. Chim. (Paris)"
    },
    {
      "key": "e_1_2_1_13_2",
      "doi-asserted-by": "crossref",
      "unstructured": "G. P.EllisandI. L.Thomas J. Chem. Soc Perkin Trans. I 2570(1974).",
      "DOI": "10.1039/p19740002570"
    },
    {
      "key": "e_1_2_1_14_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1002/jhet.5570150416"
    },
    {
      "key": "e_1_2_1_15_2",
      "volume-title": "Advances in Heterocyclic Chemistry",
      "author": "Shepherd R. G.",
      "year": "1965"
    },
    {
      "key": "e_1_2_1_15_3",
      "doi-asserted-by": "crossref",
      "unstructured": "(b)G. B.BarlinandW. V.Brown J. Chem. Soc. C 2473(1967).",
      "DOI": "10.1039/j39670002473"
    },
    {
      "key": "e_1_2_1_16_2",
      "doi-asserted-by": "crossref",
      "unstructured": "G. B.BarlinandW. V.Brown J. Chem. Soc. B 1435(1968)",
      "DOI": "10.1039/j29680001435"
    },
    {
      "key": "e_1_2_1_16_3",
      "doi-asserted-by": "publisher",
      "DOI": "10.1002/cber.19781110321"
    },
    {
      "key": "e_1_2_1_17_2",
      "doi-asserted-by": "crossref",
      "unstructured": "F. M.Dean D. B.Frankham NatiqHatamandA. W.Hill J. Chem. Soc. C 218(1971).",
      "DOI": "10.1039/j39710000218"
    },
    {
      "key": "e_1_2_1_18_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1016/S0040-4020(01)93857-8"
    },
    {
      "key": "e_1_2_1_19_2",
      "unstructured": "The pKa of 1c was 2.9 as measured spectrophotometrically."
    },
    {
      "key": "e_1_2_1_20_2",
      "doi-asserted-by": "crossref",
      "first-page": "841",
      "DOI": "10.1248/yakushi1947.96.7_841",
      "volume": "96",
      "author": "Komiya T.",
      "year": "1976",
      "journal-title": "Yakugaku Zasshi"
    },
    {
      "key": "e_1_2_1_20_3",
      "first-page": "89536a",
      "volume": "86",
      "year": "1977",
      "journal-title": "Chem. Abstr."
    },
    {
      "key": "e_1_2_1_20_4",
      "doi-asserted-by": "publisher",
      "DOI": "10.3987/R-1977-09-1581"
    },
    {
      "key": "e_1_2_1_20_5",
      "doi-asserted-by": "crossref",
      "unstructured": "(c)E. K.AdesoganandA. L.Okunade J. Chem. Soc. Chem. Commun. 152(1978).",
      "DOI": "10.1039/c39780000152"
    },
    {
      "key": "e_1_2_1_21_2",
      "unstructured": "See for example R. B.King J. C.CloydandP. N.Kapoor J. Chem. Soc. Perkin Trans. I 2226(1973)."
    },
    {
      "key": "e_1_2_1_22_2",
      "first-page": "483",
      "volume": "26",
      "author": "Cieslak J.",
      "year": "1952",
      "journal-title": "Rocz. Chem."
    },
    {
      "key": "e_1_2_1_23_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1139/v78-292"
    },
    {
      "key": "e_1_2_1_24_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/jo00807a028"
    }
  ],
  "container-title": "Journal of Heterocyclic Chemistry",
  "original-title": [],
  "language": "en",
  "link": [
    {
      "URL": "https://api.wiley.com/onlinelibrary/tdm/v1/articles/10.1002%2Fjhet.5570180407",
      "content-type": "unspecified",
      "content-version": "vor",
      "intended-application": "text-mining"
    },
    {
      "URL": "https://onlinelibrary.wiley.com/doi/pdf/10.1002/jhet.5570180407",
      "content-type": "unspecified",
      "content-version": "vor",
      "intended-application": "similarity-checking"
    }
  ],
  "deposited": {
    "date-parts": [
      [
        2023,
        11,
        6
      ]
    ],
    "date-time": "2023-11-06T15:25:20Z",
    "timestamp": 1699284320000
  },
  "score": 1,
  "resource": {
    "primary": {
      "URL": "https://onlinelibrary.wiley.com/doi/10.1002/jhet.5570180407"
    }
  },
  "subtitle": [],
  "short-title": [],
  "issued": {
    "date-parts": [
      [
        1981,
        6
      ]
    ]
  },
  "references-count": 36,
  "journal-issue": {
    "issue": "4",
    "published-print": {
      "date-parts": [
        [
          1981,
          6
        ]
      ]
    }
  },
  "alternative-id": [
    "10.1002/jhet.5570180407"
  ],
  "URL": "http://dx.doi.org/10.1002/jhet.5570180407",
  "relation": {},
  "ISSN": [
    "0022-152X",
    "1943-5193"
  ],
  "subject": [],
  "container-title-short": "Journal of Heterocyclic Chem",
  "published": {
    "date-parts": [
      [
        1981,
        6
      ]
    ]
  }
}