1, 3-Dipolar cycloaddition of 3-alkylsulfanyl-2-arylazo-3-(tert-cycloalkylamino)acrylonitriles with N-methyl- and N-phenylmaleimides. Issue 9 (4th March 2015)

• Record Type: Journal Article
• Authors: Belskaya, Nataliya P.; Lesogorova, Svetlana G.; Subbotina, Julia O.; Koksharov, Aleksandr V.; Slepukhin, Pavel A.; Dehaen, Wim; Bakulev, Vasiliy A.
• Is Part Of: Tetrahedron. Volume 71:Issue 9(2015)
• Page Start: 1438
• Page End: 1447
• Publication Date: 2015-03-04
• Subjects: Diazadiene -- S, N-Acetal -- Cycloaddition -- Maleimide -- Azomethine ylide; JKSUOEXGIKIUAT-MJIJVTJDSA-N -- YTXFPISRUGANIE-VRUOMWOPSA-N -- QIPFZFNDVXKNIJ-MJIJVTJDSA-N -- BRYZQIBUDQRLKD-DQRBBIAISA-N -- HLSHQIZSSNTSHG-QUJVQNLCSA-N -- PWWDWOLHQGFKNI-CCZOENOHSA-N -- YSLSOIKONBWJAR-PLPLIPMBSA-N -- DWFQIMVBZMHEIM-AXBBKJAMSA-N -- BKOBYUPYRIKCLI-ONURFFRRSA-N -- DASICDNQNMHAOG-ISIOZPHUSA-N -- SVPUJPRQSKZDFR-QUJVQNLCSA-N -- ANWLVDZOTUJCKH-BKUOKEKNSA-N -- JZOYIINKNRROCR-AHTWMLEKSA-N -- JFSJKMKRYYZNNC-XYRKOZFRSA-N -- VIEIUDNRGBZZCC-GZXYCKLMSA-N -- RTRNYBAHISPTMT-VRUOMWOPSA-N -- RJVCFTBOWWDQRN-SCIWZNBVSA-N -- NPCLGMGRVPVYFJ-XYRKOZFRSA-N -- SDRVBXZZFJELQZ-WWHMVCCTSA-N -- KCLPOIDUQGWSRG-MJIJVTJDSA-N -- VJJYAORLTRVZJW-GZXYCKLMSA-N -- ZWEKDCRFQANRAN-PLPLIPMBSA-N -- FNQXBGLGWBQABM-MJIJVTJDSA-N -- ONAMPMZWOCDUBM-WWHMVCCTSA-N -- PEFYEHCTWPZSCE-QJAOKCPOSA-N -- SYBZGLJMDBALRE-MRSYYDOKSA-N -- GSJORDVSDQEUFN-MHZCYWJKSA-N -- VTBHZXWOBBMGLI-TYGDGSGYSA-N -- KEABMCLWZZJVFS-HYLZLKDASA-N -- ZUXXPYYGZFOWIJ-ONURFFRRSA-N -- PXDUVMYJCXCCTQ-AFFDJESPSA-N -- WCFWQTSYOBZYDK-BKUOKEKNSA-N -- CDVRXRGOMJXVJN-MJCYWKBOSA-N -- YOFQBIDDIQXFNG-HYLZLKDASA-N -- YUMNGDJKPTYZCZ-VRUOMWOPSA-N -- BRULUSCCFPUKTL-TYGDGSGYSA-N -- UGLXZSUUPHWNER-GZXYCKLMSA-N -- HMPWQQTYKMQSSB-AHTWMLEKSA-N -- WWSHHUGFZNZQII-XDGYYMMHSA-N -- UCIMLOJHRXNZMJ-BJFBWCCZSA-N -- RKLKFGOJAABZNW-PLPLIPMBSA-N; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tet.2014.12.087
• Languages: English
• ISSNs: 0040-4020

Abstract

Abstract: A series of 1, 2-diaza-1, 3-butadienes with terminal S, N -acetal function were obtained and reacted with N -methyl- and N -phenylmaleimides. As a result of the 1, 3-dipolar cycloaddition, a range of new functionalized nonaromatic heterocyclic compounds including: octahydro-1 H -pyrrolo[3, 4- a ]indolizine, octahydropyrrolo[3′, 4′:3, 4]pyrrolo[1, 2- a ]azepine, hexahydropyrrolo[3′, 4′:3, 4]pyrrolo[2, 1- c ][1, 4]oxazine and -thiazine, were obtained with good yields in mild conditions. Experimental and theoretic results allowed establishment of a relationship between the structures of the tert -cycloalkylamine group and the activity of the azomethine ylides generated. Graphical abstract: