سنتز ایندول کداگن-ساندبرگ

سنتز ایندول کداگن-ساندبرگ
نامگذاری شده پس از	جان کداگن; ریچارد جی. ساندبرگ
نوع واکنش	واکنش‌های تشکیل حلقه
شناسه‌ها
RSC ontology ID	RXNO:0000509

سنتز ایندول کداگن-ساندبرگ (به انگلیسی: Cadogan-Sundberg indole synthesis)، یا به شکل ساده سنتز ایندول کداگن، یک نام واکنش در شیمی آلی است که امکان تولید ایندول از اورتو-نیترواستایرن‌ها با استفاده از تری‌آلکیل فسفیت‌ها، مانند تری‌اتیل فسفیت را فراهم می‌سازد.^[۱]^[۲]^[۳]^[۴]^[۵]^[۶]^[۷]

سازوکار[ویرایش]

ابتدا اورتو-نیترواستایرن با تری‌اتیل فسفیت واکنش می‌دهد و گروه نیترو به یک گروه نیتروزو تبدیل می‌شود. سپس گروه نیتروزو با آلکن واکنش می‌دهد و N-هیدروکسیل‌ایندول تشکیل می‌شود که دوباره با تری‌اتیل فسفیت واکنش داده و ایندول را تشکیل می‌دهد.^[۸]^[۹]^[۱۰]^[۱۱]

کاربرد[ویرایش]

سنتز ایندول کداگن-ساندبرگ به عنوان یک مرحله میانی در سنتز جامع Tjipanazole E استفاده می‌شود.^[۱۲]

منابع[ویرایش]

↑ Cadogan, John Ivan George; Mackie, R. K. (1974). "Tervalent phosphorus compounds in organic synthesis". Chemical Society Reviews. 3 (1): 87–137. doi:10.1039/CS9740300087.
↑ Wang, Zerong (15 September 2010). Comprehensive Organic Name Reactions and Reagents. doi:10.1002/9780470638859.conrr128. ISBN 9780470638859.
↑ Sundberg, Richard J.; Yamazaki, Toshio (1 February 1967). "Rearrangements and ring expansions during the deoxygenation of β,β-disubstituted o-nitrostyrenes". The Journal of Organic Chemistry. 32 (2): 290–294. doi:10.1021/jo01288a009.
↑ Sundberg, Richard J. (1 November 1965). "Deoxygenation of Nitro Groups by Trivalent Phosphorus. Indoles from o-Nitrostyrenes". The Journal of Organic Chemistry. 30 (11): 3604–3610. doi:10.1021/jo01022a006.
↑ Gribble, Gordon W. (17 June 2016). "Cadogan–Sundberg Indole Synthesis". Indole Ring Synthesis: From Natural Products to Drug Discovery. doi:10.1002/9781118695692.ch26. ISBN 9781118695692.
↑ Majgier-Baranowska, Helena; Williams, John D.; Li, Bing; Peet, Norton P. (1 February 1967). "Studies on the mechanism of the Cadogan–Sundberg indole synthesis". Tetrahedron Letters. 53 (35): 4785–4788. doi:10.1016/j.tetlet.2012.06.146.
↑ Li, Jie Jack (4 January 2014). "Cadogan–Sundberg indole synthesis". Indole Ring Synthesis: From Natural Products to Drug Discovery. Springer. p. 102-103. doi:10.1007/978-3-319-03979-4_49. ISBN 978-3-319-03979-4.
↑ Cadogan, John Ivan George; Mackie, R. K. (1974). "Tervalent phosphorus compounds in organic synthesis". Chemical Society Reviews. 3 (1): 87–137. doi:10.1039/CS9740300087.
↑ Wang, Zerong (15 September 2010). Comprehensive Organic Name Reactions and Reagents. doi:10.1002/9780470638859.conrr128. ISBN 9780470638859.
↑ Sundberg, Richard J.; Yamazaki, Toshio (1 February 1967). "Rearrangements and ring expansions during the deoxygenation of β,β-disubstituted o-nitrostyrenes". The Journal of Organic Chemistry. 32 (2): 290–294. doi:10.1021/jo01288a009.
↑ Sundberg, Richard J. (1 November 1965). "Deoxygenation of Nitro Groups by Trivalent Phosphorus. Indoles from o-Nitrostyrenes". The Journal of Organic Chemistry. 30 (11): 3604–3610. doi:10.1021/jo01022a006.
↑ Kuethe, Jeffrey T.; Wong, Audrey; Davies, Iaan W. (3 September 2003). "Effective Strategy for the Preparation of Indolocarbazole Aglycons and Glycosides: Total Synthesis of Tjipanazoles B, D, E, and I". Organic Letters. 5 (20): 3721–3723. doi:10.1021/ol035418r.

[Cadogan2-1] Cadogan, John Ivan George; Mackie, R. K. (1974). "Tervalent phosphorus compounds in organic synthesis". Chemical Society Reviews. 3 (1): 87–137. doi:10.1039/CS9740300087.

[Wang2-2] Wang, Zerong (15 September 2010). Comprehensive Organic Name Reactions and Reagents. doi:10.1002/9780470638859.conrr128. ISBN 9780470638859.

[Yamazaki2-3] Sundberg, Richard J.; Yamazaki, Toshio (1 February 1967). "Rearrangements and ring expansions during the deoxygenation of β,β-disubstituted o-nitrostyrenes". The Journal of Organic Chemistry. 32 (2): 290–294. doi:10.1021/jo01288a009.

[Sundberg2-4] Sundberg, Richard J. (1 November 1965). "Deoxygenation of Nitro Groups by Trivalent Phosphorus. Indoles from o-Nitrostyrenes". The Journal of Organic Chemistry. 30 (11): 3604–3610. doi:10.1021/jo01022a006.

[Gribble2-5] Gribble, Gordon W. (17 June 2016). "Cadogan–Sundberg Indole Synthesis". Indole Ring Synthesis: From Natural Products to Drug Discovery. doi:10.1002/9781118695692.ch26. ISBN 9781118695692.

[Tetrahedron2-6] Majgier-Baranowska, Helena; Williams, John D.; Li, Bing; Peet, Norton P. (1 February 1967). "Studies on the mechanism of the Cadogan–Sundberg indole synthesis". Tetrahedron Letters. 53 (35): 4785–4788. doi:10.1016/j.tetlet.2012.06.146.

[Li_Name_Reactions2-7] Li, Jie Jack (4 January 2014). "Cadogan–Sundberg indole synthesis". Indole Ring Synthesis: From Natural Products to Drug Discovery. Springer. p. 102-103. doi:10.1007/978-3-319-03979-4_49. ISBN 978-3-319-03979-4.

[Cadogan3-8] Cadogan, John Ivan George; Mackie, R. K. (1974). "Tervalent phosphorus compounds in organic synthesis". Chemical Society Reviews. 3 (1): 87–137. doi:10.1039/CS9740300087.

[Wang3-9] Wang, Zerong (15 September 2010). Comprehensive Organic Name Reactions and Reagents. doi:10.1002/9780470638859.conrr128. ISBN 9780470638859.

[Yamazaki3-10] Sundberg, Richard J.; Yamazaki, Toshio (1 February 1967). "Rearrangements and ring expansions during the deoxygenation of β,β-disubstituted o-nitrostyrenes". The Journal of Organic Chemistry. 32 (2): 290–294. doi:10.1021/jo01288a009.

[Sundberg3-11] Sundberg, Richard J. (1 November 1965). "Deoxygenation of Nitro Groups by Trivalent Phosphorus. Indoles from o-Nitrostyrenes". The Journal of Organic Chemistry. 30 (11): 3604–3610. doi:10.1021/jo01022a006.

[12] Kuethe, Jeffrey T.; Wong, Audrey; Davies, Iaan W. (3 September 2003). "Effective Strategy for the Preparation of Indolocarbazole Aglycons and Glycosides: Total Synthesis of Tjipanazoles B, D, E, and I". Organic Letters. 5 (20): 3721–3723. doi:10.1021/ol035418r.

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