DBU-Mediated Reaction of 3-Chlorooxindole and 9-Xanthyl Fluorene for Synthesis of 3-Arylidene Oxindole

Nitchakan Purahong; Thapong Teerawatananond; Nawasit Chotsaeng; Pattarapapa Janthakit; Phattananawee Nalaoh; Vinich Promarak; Chutima Kuhakarn; Jatuporn Meesin

doi:10.1002/ajoc.202400660

DBU-Mediated Reaction of 3-Chlorooxindole and 9-Xanthyl Fluorene for Synthesis of 3-Arylidene Oxindole

Nitchakan Purahong
, Thapong Teerawatananond
, Nawasit Chotsaeng
, Pattarapapa Janthakit
, Phattananawee Nalaoh
, Vinich Promarak
, Chutima Kuhakarn
, Jatuporn Meesin

King Mongkut's Institute of Technology Ladkrabang
Vidyasirimedhi Institute of Science and Technology
Mahidol University

Research output: Contribution to journal › Article › peer-review

3 Citations (Scopus)

Abstract

This work reports a new route for the synthesis of 3-(9H-fluoren-9-ylidene)indolin-2-one derivatives via the reaction of 3-chlorooxindoles and O-ethyl S-(9H-fluoren-9-yl) carbonodithioates mediated by 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU). The reactions readily proceeded at room temperature, enable a collection of 3-alkenyl oxindoles to be prepared within a short reaction time (15 minutes). The 3-alkenyl oxindoles can be easily converted to 3-fluorenyl oxindoles by NaBH₄ reduction.

Original language	English
Article number	e202400660
Journal	Asian Journal of Organic Chemistry
Volume	14
Issue number	4
DOIs	https://doi.org/10.1002/ajoc.202400660
Publication status	Published - Apr 2025
Externally published	Yes

Keywords

3-Alkenyl-oxindoles
3-Chloroindolin-2-one
DBU
O-ethyl S-(9H-fluoren-9-yl) carbonodithioate
cross-coupling

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10.1002/ajoc.202400660

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title = "DBU-Mediated Reaction of 3-Chlorooxindole and 9-Xanthyl Fluorene for Synthesis of 3-Arylidene Oxindole",

abstract = "This work reports a new route for the synthesis of 3-(9H-fluoren-9-ylidene)indolin-2-one derivatives via the reaction of 3-chlorooxindoles and O-ethyl S-(9H-fluoren-9-yl) carbonodithioates mediated by 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU). The reactions readily proceeded at room temperature, enable a collection of 3-alkenyl oxindoles to be prepared within a short reaction time (15 minutes). The 3-alkenyl oxindoles can be easily converted to 3-fluorenyl oxindoles by NaBH4 reduction.",

keywords = "3-Alkenyl-oxindoles, 3-Chloroindolin-2-one, DBU, O-ethyl S-(9H-fluoren-9-yl) carbonodithioate, cross-coupling",

author = "Nitchakan Purahong and Thapong Teerawatananond and Nawasit Chotsaeng and Pattarapapa Janthakit and Phattananawee Nalaoh and Vinich Promarak and Chutima Kuhakarn and Jatuporn Meesin",

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doi = "10.1002/ajoc.202400660",

language = "English",

volume = "14",

journal = "Asian Journal of Organic Chemistry",

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T1 - DBU-Mediated Reaction of 3-Chlorooxindole and 9-Xanthyl Fluorene for Synthesis of 3-Arylidene Oxindole

AU - Purahong, Nitchakan

AU - Teerawatananond, Thapong

AU - Chotsaeng, Nawasit

AU - Janthakit, Pattarapapa

AU - Nalaoh, Phattananawee

AU - Promarak, Vinich

AU - Kuhakarn, Chutima

AU - Meesin, Jatuporn

PY - 2025/4

Y1 - 2025/4

N2 - This work reports a new route for the synthesis of 3-(9H-fluoren-9-ylidene)indolin-2-one derivatives via the reaction of 3-chlorooxindoles and O-ethyl S-(9H-fluoren-9-yl) carbonodithioates mediated by 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU). The reactions readily proceeded at room temperature, enable a collection of 3-alkenyl oxindoles to be prepared within a short reaction time (15 minutes). The 3-alkenyl oxindoles can be easily converted to 3-fluorenyl oxindoles by NaBH4 reduction.

AB - This work reports a new route for the synthesis of 3-(9H-fluoren-9-ylidene)indolin-2-one derivatives via the reaction of 3-chlorooxindoles and O-ethyl S-(9H-fluoren-9-yl) carbonodithioates mediated by 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU). The reactions readily proceeded at room temperature, enable a collection of 3-alkenyl oxindoles to be prepared within a short reaction time (15 minutes). The 3-alkenyl oxindoles can be easily converted to 3-fluorenyl oxindoles by NaBH4 reduction.

KW - 3-Alkenyl-oxindoles

KW - 3-Chloroindolin-2-one

KW - DBU

KW - O-ethyl S-(9H-fluoren-9-yl) carbonodithioate

KW - cross-coupling

UR - https://www.scopus.com/pages/publications/105002990104

U2 - 10.1002/ajoc.202400660

DO - 10.1002/ajoc.202400660

M3 - Article

AN - SCOPUS:105002990104

SN - 2193-5807

VL - 14

JO - Asian Journal of Organic Chemistry

JF - Asian Journal of Organic Chemistry

IS - 4

M1 - e202400660

ER -

DBU-Mediated Reaction of 3-Chlorooxindole and 9-Xanthyl Fluorene for Synthesis of 3-Arylidene Oxindole

Abstract

Keywords

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