Sequential cyclizations of 2-isothiocyanatobenzonitrile with α-amino-carboxylic esters and acids

Synlett

Volumn , Issue 11, 2003, Pages 1743-1745

  Langer, Peter ^a   Bodtke, Anja ^a  

^a UNIVERSITY OF GREIFSWALD   (Germany)

Author keywords

Amino acids; Cyclizations; Domino reactions; Isothiocyanates; Regioselectivity

Indexed keywords

2 ISOTHIOCYANATOBENZONITRILE; BENZONITRILE; CARBOXYLIC ACID DERIVATIVE; ESTER DERIVATIVE; QUINAZOLINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL MODIFICATION; CYCLIZATION; DRUG SYNTHESIS; STEREOCHEMISTRY;

EID: 0041409628     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2003-41435     Document Type: Article

References (29)

1. For reviews of domino and sequential reactions, see: (a) Tietze, L. F.; Beifuss, U. Angew. Chem., Int. Ed. Engl. 1993, 32, 131; Angew. Chem. 1993, 105, 137. (b) Tietze, L. F. Chem. Rev. 1996, 96, 115.
2. For reviews of domino and sequential reactions, see: (a) Tietze, L. F.; Beifuss, U. Angew. Chem., Int. Ed. Engl. 1993, 32, 131; Angew. Chem. 1993, 105, 137. (b) Tietze, L. F. Chem. Rev. 1996, 96, 115.
3. For reviews of work from our laboratory, see: (a) Langer, P. Chem.-Eur. J. 2001, 7, 3858. (b) Langer, P.; Döring, M. Eur. J. Org. Chem. 2002, 221. (c) Langer, P. Synthesis 2002, 441.
4. For reviews of work from our laboratory, see: (a) Langer, P. Chem.-Eur. J. 2001, 7, 3858. (b) Langer, P.; Döring, M. Eur. J. Org. Chem. 2002, 221. (c) Langer, P. Synthesis 2002, 441.
5. For reviews of work from our laboratory, see: (a) Langer, P. Chem.-Eur. J. 2001, 7, 3858. (b) Langer, P.; Döring, M. Eur. J. Org. Chem. 2002, 221. (c) Langer, P. Synthesis 2002, 441.
6. For the synthesis of open-chained products: (a) Besson, T.; Guillard, J. ; Rees, C. W.; Therisod, M. Chem. Commun. 1997, 881. (b) Leardini, R.; Nanni, D.; Pareschi, P.; Tundo, A.; Zanardi, G. J. Org. Chem. 1997, 62, 8394. (c) Pavia, M. R.; Lobbestael, S. J.; Taylor, C. P.; Hershenson, F. M.; Miskell, D. L. J. Med. Chem. 1990, 33, 854. (d) For the synthesis of 1a: Pfeiffer, W. D.; Pazdera, P.; Hetzheim, A.; Muecke, J. Pharmazie 1995, 50, 21. (e) For cyclizations with hydrazine: Pfeiffer, W.-D.; Hetzheim, A.; Pazdera, P.; Bodtke, A.; Mücke, J. J. Heterocycl. Chem. 1999, 36, 1327. (f) For reactions with carboxylic hydrazides: Francis, J. E.; Cash, W. D.; Psychoyos, S.; Ghai, G.; Wenk, P.; Friedmann, R. C.; Atkins, C.; Warren, V.; Furness, P.; Hyun, J. L.; Stone, G. A.; Desai, M.; Williams, M. J. Med. Chem. 1988, 31, 1014. (g) Also see: Blank, J.; Kandt, M.; Pfeiffer, W.-D.; Hetzheim, A.; Langer, P. Eur. J. Org. Chem. 2003, 182.(h) For cyclization reactions with aminoketones: Thom, A.; Zinner, G. Arch. Pharm. (Weinheim, Ger.) 1994, 327, 469. (i) See also:Langer, P.; Bodtke, A. Tetrahedron Lett. 2003, 44, 5965. (j) For reactions with nitrile and malonate carbanions: Langer, P.; Albrecht, U. Synlett. 2003, 1503. (k) For an oxidative dimerization: Calestani, G.; Capella, L.; Leardini, R.; Minozzi, M.; Nanni, D.; Papa, R.; Romina, R.; Zanardi, G. Tetrahedron 2001, 57, 7221.
7. For the synthesis of open-chained products: (a) Besson, T.; Guillard, J. ; Rees, C. W.; Therisod, M. Chem. Commun. 1997, 881. (b) Leardini, R.; Nanni, D.; Pareschi, P.; Tundo, A.; Zanardi, G. J. Org. Chem. 1997, 62, 8394. (c) Pavia, M. R.; Lobbestael, S. J.; Taylor, C. P.; Hershenson, F. M.; Miskell, D. L. J. Med. Chem. 1990, 33, 854. (d) For the synthesis of 1a: Pfeiffer, W. D.; Pazdera, P.; Hetzheim, A.; Muecke, J. Pharmazie 1995, 50, 21. (e) For cyclizations with hydrazine: Pfeiffer, W.-D.; Hetzheim, A.; Pazdera, P.; Bodtke, A.; Mücke, J. J. Heterocycl. Chem. 1999, 36, 1327. (f) For reactions with carboxylic hydrazides: Francis, J. E.; Cash, W. D.; Psychoyos, S.; Ghai, G.; Wenk, P.; Friedmann, R. C.; Atkins, C.; Warren, V.; Furness, P.; Hyun, J. L.; Stone, G. A.; Desai, M.; Williams, M. J. Med. Chem. 1988, 31, 1014. (g) Also see: Blank, J.; Kandt, M.; Pfeiffer, W.-D.; Hetzheim, A.; Langer, P. Eur. J. Org. Chem. 2003, 182.(h) For cyclization reactions with aminoketones: Thom, A.; Zinner, G. Arch. Pharm. (Weinheim, Ger.) 1994, 327, 469. (i) See also:Langer, P.; Bodtke, A. Tetrahedron Lett. 2003, 44, 5965. (j) For reactions with nitrile and malonate carbanions: Langer, P.; Albrecht, U. Synlett. 2003, 1503. (k) For an oxidative dimerization: Calestani, G.; Capella, L.; Leardini, R.; Minozzi, M.; Nanni, D.; Papa, R.; Romina, R.; Zanardi, G. Tetrahedron 2001, 57, 7221.
8. For the synthesis of open-chained products: (a) Besson, T.; Guillard, J. ; Rees, C. W.; Therisod, M. Chem. Commun. 1997, 881. (b) Leardini, R.; Nanni, D.; Pareschi, P.; Tundo, A.; Zanardi, G. J. Org. Chem. 1997, 62, 8394. (c) Pavia, M. R.; Lobbestael, S. J.; Taylor, C. P.; Hershenson, F. M.; Miskell, D. L. J. Med. Chem. 1990, 33, 854. (d) For the synthesis of 1a: Pfeiffer, W. D.; Pazdera, P.; Hetzheim, A.; Muecke, J. Pharmazie 1995, 50, 21. (e) For cyclizations with hydrazine: Pfeiffer, W.-D.; Hetzheim, A.; Pazdera, P.; Bodtke, A.; Mücke, J. J. Heterocycl. Chem. 1999, 36, 1327. (f) For reactions with carboxylic hydrazides: Francis, J. E.; Cash, W. D.; Psychoyos, S.; Ghai, G.; Wenk, P.; Friedmann, R. C.; Atkins, C.; Warren, V.; Furness, P.; Hyun, J. L.; Stone, G. A.; Desai, M.; Williams, M. J. Med. Chem. 1988, 31, 1014. (g) Also see: Blank, J.; Kandt, M.; Pfeiffer, W.-D.; Hetzheim, A.; Langer, P. Eur. J. Org. Chem. 2003, 182.(h) For cyclization reactions with aminoketones: Thom, A.; Zinner, G. Arch. Pharm. (Weinheim, Ger.) 1994, 327, 469. (i) See also:Langer, P.; Bodtke, A. Tetrahedron Lett. 2003, 44, 5965. (j) For reactions with nitrile and malonate carbanions: Langer, P.; Albrecht, U. Synlett. 2003, 1503. (k) For an oxidative dimerization: Calestani, G.; Capella, L.; Leardini, R.; Minozzi, M.; Nanni, D.; Papa, R.; Romina, R.; Zanardi, G. Tetrahedron 2001, 57, 7221.
9. For the synthesis of open-chained products: (a) Besson, T.; Guillard, J. ; Rees, C. W.; Therisod, M. Chem. Commun. 1997, 881. (b) Leardini, R.; Nanni, D.; Pareschi, P.; Tundo, A.; Zanardi, G. J. Org. Chem. 1997, 62, 8394. (c) Pavia, M. R.; Lobbestael, S. J.; Taylor, C. P.; Hershenson, F. M.; Miskell, D. L. J. Med. Chem. 1990, 33, 854. (d) For the synthesis of 1a: Pfeiffer, W. D.; Pazdera, P.; Hetzheim, A.; Muecke, J. Pharmazie 1995, 50, 21. (e) For cyclizations with hydrazine: Pfeiffer, W.-D.; Hetzheim, A.; Pazdera, P.; Bodtke, A.; Mücke, J. J. Heterocycl. Chem. 1999, 36, 1327. (f) For reactions with carboxylic hydrazides: Francis, J. E.; Cash, W. D.; Psychoyos, S.; Ghai, G.; Wenk, P.; Friedmann, R. C.; Atkins, C.; Warren, V.; Furness, P.; Hyun, J. L.; Stone, G. A.; Desai, M.; Williams, M. J. Med. Chem. 1988, 31, 1014. (g) Also see: Blank, J.; Kandt, M.; Pfeiffer, W.-D.; Hetzheim, A.; Langer, P. Eur. J. Org. Chem. 2003, 182.(h) For cyclization reactions with aminoketones: Thom, A.; Zinner, G. Arch. Pharm. (Weinheim, Ger.) 1994, 327, 469. (i) See also:Langer, P.; Bodtke, A. Tetrahedron Lett. 2003, 44, 5965. (j) For reactions with nitrile and malonate carbanions: Langer, P.; Albrecht, U. Synlett. 2003, 1503. (k) For an oxidative dimerization: Calestani, G.; Capella, L.; Leardini, R.; Minozzi, M.; Nanni, D.; Papa, R.; Romina, R.; Zanardi, G. Tetrahedron 2001, 57, 7221.
10. For the synthesis of open-chained products: (a) Besson, T.; Guillard, J. ; Rees, C. W.; Therisod, M. Chem. Commun. 1997, 881. (b) Leardini, R.; Nanni, D.; Pareschi, P.; Tundo, A.; Zanardi, G. J. Org. Chem. 1997, 62, 8394. (c) Pavia, M. R.; Lobbestael, S. J.; Taylor, C. P.; Hershenson, F. M.; Miskell, D. L. J. Med. Chem. 1990, 33, 854. (d) For the synthesis of 1a: Pfeiffer, W. D.; Pazdera, P.; Hetzheim, A.; Muecke, J. Pharmazie 1995, 50, 21. (e) For cyclizations with hydrazine: Pfeiffer, W.-D.; Hetzheim, A.; Pazdera, P.; Bodtke, A.; Mücke, J. J. Heterocycl. Chem. 1999, 36, 1327. (f) For reactions with carboxylic hydrazides: Francis, J. E.; Cash, W. D.; Psychoyos, S.; Ghai, G.; Wenk, P.; Friedmann, R. C.; Atkins, C.; Warren, V.; Furness, P.; Hyun, J. L.; Stone, G. A.; Desai, M.; Williams, M. J. Med. Chem. 1988, 31, 1014. (g) Also see: Blank, J.; Kandt, M.; Pfeiffer, W.-D.; Hetzheim, A.; Langer, P. Eur. J. Org. Chem. 2003, 182.(h) For cyclization reactions with aminoketones: Thom, A.; Zinner, G. Arch. Pharm. (Weinheim, Ger.) 1994, 327, 469. (i) See also:Langer, P.; Bodtke, A. Tetrahedron Lett. 2003, 44, 5965. (j) For reactions with nitrile and malonate carbanions: Langer, P.; Albrecht, U. Synlett. 2003, 1503. (k) For an oxidative dimerization: Calestani, G.; Capella, L.; Leardini, R.; Minozzi, M.; Nanni, D.; Papa, R.; Romina, R.; Zanardi, G. Tetrahedron 2001, 57, 7221.
11. For the synthesis of open-chained products: (a) Besson, T.; Guillard, J. ; Rees, C. W.; Therisod, M. Chem. Commun. 1997, 881. (b) Leardini, R.; Nanni, D.; Pareschi, P.; Tundo, A.; Zanardi, G. J. Org. Chem. 1997, 62, 8394. (c) Pavia, M. R.; Lobbestael, S. J.; Taylor, C. P.; Hershenson, F. M.; Miskell, D. L. J. Med. Chem. 1990, 33, 854. (d) For the synthesis of 1a: Pfeiffer, W. D.; Pazdera, P.; Hetzheim, A.; Muecke, J. Pharmazie 1995, 50, 21. (e) For cyclizations with hydrazine: Pfeiffer, W.-D.; Hetzheim, A.; Pazdera, P.; Bodtke, A.; Mücke, J. J. Heterocycl. Chem. 1999, 36, 1327. (f) For reactions with carboxylic hydrazides: Francis, J. E.; Cash, W. D.; Psychoyos, S.; Ghai, G.; Wenk, P.; Friedmann, R. C.; Atkins, C.; Warren, V.; Furness, P.; Hyun, J. L.; Stone, G. A.; Desai, M.; Williams, M. J. Med. Chem. 1988, 31, 1014. (g) Also see: Blank, J.; Kandt, M.; Pfeiffer, W.-D.; Hetzheim, A.; Langer, P. Eur. J. Org. Chem. 2003, 182.(h) For cyclization reactions with aminoketones: Thom, A.; Zinner, G. Arch. Pharm. (Weinheim, Ger.) 1994, 327, 469. (i) See also:Langer, P.; Bodtke, A. Tetrahedron Lett. 2003, 44, 5965. (j) For reactions with nitrile and malonate carbanions: Langer, P.; Albrecht, U. Synlett. 2003, 1503. (k) For an oxidative dimerization: Calestani, G.; Capella, L.; Leardini, R.; Minozzi, M.; Nanni, D.; Papa, R.; Romina, R.; Zanardi, G. Tetrahedron 2001, 57, 7221.
12. For the synthesis of open-chained products: (a) Besson, T.; Guillard, J. ; Rees, C. W.; Therisod, M. Chem. Commun. 1997, 881. (b) Leardini, R.; Nanni, D.; Pareschi, P.; Tundo, A.; Zanardi, G. J. Org. Chem. 1997, 62, 8394. (c) Pavia, M. R.; Lobbestael, S. J.; Taylor, C. P.; Hershenson, F. M.; Miskell, D. L. J. Med. Chem. 1990, 33, 854. (d) For the synthesis of 1a: Pfeiffer, W. D.; Pazdera, P.; Hetzheim, A.; Muecke, J. Pharmazie 1995, 50, 21. (e) For cyclizations with hydrazine: Pfeiffer, W.-D.; Hetzheim, A.; Pazdera, P.; Bodtke, A.; Mücke, J. J. Heterocycl. Chem. 1999, 36, 1327. (f) For reactions with carboxylic hydrazides: Francis, J. E.; Cash, W. D.; Psychoyos, S.; Ghai, G.; Wenk, P.; Friedmann, R. C.; Atkins, C.; Warren, V.; Furness, P.; Hyun, J. L.; Stone, G. A.; Desai, M.; Williams, M. J. Med. Chem. 1988, 31, 1014. (g) Also see: Blank, J.; Kandt, M.; Pfeiffer, W.-D.; Hetzheim, A.; Langer, P. Eur. J. Org. Chem. 2003, 182.(h) For cyclization reactions with aminoketones: Thom, A.; Zinner, G. Arch. Pharm. (Weinheim, Ger.) 1994, 327, 469. (i) See also:Langer, P.; Bodtke, A. Tetrahedron Lett. 2003, 44, 5965. (j) For reactions with nitrile and malonate carbanions: Langer, P.; Albrecht, U. Synlett. 2003, 1503. (k) For an oxidative dimerization: Calestani, G.; Capella, L.; Leardini, R.; Minozzi, M.; Nanni, D.; Papa, R.; Romina, R.; Zanardi, G. Tetrahedron 2001, 57, 7221.
13. For the synthesis of open-chained products: (a) Besson, T.; Guillard, J. ; Rees, C. W.; Therisod, M. Chem. Commun. 1997, 881. (b) Leardini, R.; Nanni, D.; Pareschi, P.; Tundo, A.; Zanardi, G. J. Org. Chem. 1997, 62, 8394. (c) Pavia, M. R.; Lobbestael, S. J.; Taylor, C. P.; Hershenson, F. M.; Miskell, D. L. J. Med. Chem. 1990, 33, 854. (d) For the synthesis of 1a: Pfeiffer, W. D.; Pazdera, P.; Hetzheim, A.; Muecke, J. Pharmazie 1995, 50, 21. (e) For cyclizations with hydrazine: Pfeiffer, W.-D.; Hetzheim, A.; Pazdera, P.; Bodtke, A.; Mücke, J. J. Heterocycl. Chem. 1999, 36, 1327. (f) For reactions with carboxylic hydrazides: Francis, J. E.; Cash, W. D.; Psychoyos, S.; Ghai, G.; Wenk, P.; Friedmann, R. C.; Atkins, C.; Warren, V.; Furness, P.; Hyun, J. L.; Stone, G. A.; Desai, M.; Williams, M. J. Med. Chem. 1988, 31, 1014. (g) Also see: Blank, J.; Kandt, M.; Pfeiffer, W.-D.; Hetzheim, A.; Langer, P. Eur. J. Org. Chem. 2003, 182.(h) For cyclization reactions with aminoketones: Thom, A.; Zinner, G. Arch. Pharm. (Weinheim, Ger.) 1994, 327, 469. (i) See also:Langer, P.; Bodtke, A. Tetrahedron Lett. 2003, 44, 5965. (j) For reactions with nitrile and malonate carbanions: Langer, P.; Albrecht, U. Synlett. 2003, 1503. (k) For an oxidative dimerization: Calestani, G.; Capella, L.; Leardini, R.; Minozzi, M.; Nanni, D.; Papa, R.; Romina, R.; Zanardi, G. Tetrahedron 2001, 57, 7221.
14. For the synthesis of open-chained products: (a) Besson, T.; Guillard, J. ; Rees, C. W.; Therisod, M. Chem. Commun. 1997, 881. (b) Leardini, R.; Nanni, D.; Pareschi, P.; Tundo, A.; Zanardi, G. J. Org. Chem. 1997, 62, 8394. (c) Pavia, M. R.; Lobbestael, S. J.; Taylor, C. P.; Hershenson, F. M.; Miskell, D. L. J. Med. Chem. 1990, 33, 854. (d) For the synthesis of 1a: Pfeiffer, W. D.; Pazdera, P.; Hetzheim, A.; Muecke, J. Pharmazie 1995, 50, 21. (e) For cyclizations with hydrazine: Pfeiffer, W.-D.; Hetzheim, A.; Pazdera, P.; Bodtke, A.; Mücke, J. J. Heterocycl. Chem. 1999, 36, 1327. (f) For reactions with carboxylic hydrazides: Francis, J. E.; Cash, W. D.; Psychoyos, S.; Ghai, G.; Wenk, P.; Friedmann, R. C.; Atkins, C.; Warren, V.; Furness, P.; Hyun, J. L.; Stone, G. A.; Desai, M.; Williams, M. J. Med. Chem. 1988, 31, 1014. (g) Also see: Blank, J.; Kandt, M.; Pfeiffer, W.-D.; Hetzheim, A.; Langer, P. Eur. J. Org. Chem. 2003, 182.(h) For cyclization reactions with aminoketones: Thom, A.; Zinner, G. Arch. Pharm. (Weinheim, Ger.) 1994, 327, 469. (i) See also:Langer, P.; Bodtke, A. Tetrahedron Lett. 2003, 44, 5965. (j) For reactions with nitrile and malonate carbanions: Langer, P.; Albrecht, U. Synlett. 2003, 1503. (k) For an oxidative dimerization: Calestani, G.; Capella, L.; Leardini, R.; Minozzi, M.; Nanni, D.; Papa, R.; Romina, R.; Zanardi, G. Tetrahedron 2001, 57, 7221.
15. For the synthesis of open-chained products: (a) Besson, T.; Guillard, J. ; Rees, C. W.; Therisod, M. Chem. Commun. 1997, 881. (b) Leardini, R.; Nanni, D.; Pareschi, P.; Tundo, A.; Zanardi, G. J. Org. Chem. 1997, 62, 8394. (c) Pavia, M. R.; Lobbestael, S. J.; Taylor, C. P.; Hershenson, F. M.; Miskell, D. L. J. Med. Chem. 1990, 33, 854. (d) For the synthesis of 1a: Pfeiffer, W. D.; Pazdera, P.; Hetzheim, A.; Muecke, J. Pharmazie 1995, 50, 21. (e) For cyclizations with hydrazine: Pfeiffer, W.-D.; Hetzheim, A.; Pazdera, P.; Bodtke, A.; Mücke, J. J. Heterocycl. Chem. 1999, 36, 1327. (f) For reactions with carboxylic hydrazides: Francis, J. E.; Cash, W. D.; Psychoyos, S.; Ghai, G.; Wenk, P.; Friedmann, R. C.; Atkins, C.; Warren, V.; Furness, P.; Hyun, J. L.; Stone, G. A.; Desai, M.; Williams, M. J. Med. Chem. 1988, 31, 1014. (g) Also see: Blank, J.; Kandt, M.; Pfeiffer, W.-D.; Hetzheim, A.; Langer, P. Eur. J. Org. Chem. 2003, 182.(h) For cyclization reactions with aminoketones: Thom, A.; Zinner, G. Arch. Pharm. (Weinheim, Ger.) 1994, 327, 469. (i) See also:Langer, P.; Bodtke, A. Tetrahedron Lett. 2003, 44, 5965. (j) For reactions with nitrile and malonate carbanions: Langer, P.; Albrecht, U. Synlett. 2003, 1503. (k) For an oxidative dimerization: Calestani, G.; Capella, L.; Leardini, R.; Minozzi, M.; Nanni, D.; Papa, R.; Romina, R.; Zanardi, G. Tetrahedron 2001, 57, 7221.
16. For the synthesis of open-chained products: (a) Besson, T.; Guillard, J. ; Rees, C. W.; Therisod, M. Chem. Commun. 1997, 881. (b) Leardini, R.; Nanni, D.; Pareschi, P.; Tundo, A.; Zanardi, G. J. Org. Chem. 1997, 62, 8394. (c) Pavia, M. R.; Lobbestael, S. J.; Taylor, C. P.; Hershenson, F. M.; Miskell, D. L. J. Med. Chem. 1990, 33, 854. (d) For the synthesis of 1a: Pfeiffer, W. D.; Pazdera, P.; Hetzheim, A.; Muecke, J. Pharmazie 1995, 50, 21. (e) For cyclizations with hydrazine: Pfeiffer, W.-D.; Hetzheim, A.; Pazdera, P.; Bodtke, A.; Mücke, J. J. Heterocycl. Chem. 1999, 36, 1327. (f) For reactions with carboxylic hydrazides: Francis, J. E.; Cash, W. D.; Psychoyos, S.; Ghai, G.; Wenk, P.; Friedmann, R. C.; Atkins, C.; Warren, V.; Furness, P.; Hyun, J. L.; Stone, G. A.; Desai, M.; Williams, M. J. Med. Chem. 1988, 31, 1014. (g) Also see: Blank, J.; Kandt, M.; Pfeiffer, W.-D.; Hetzheim, A.; Langer, P. Eur. J. Org. Chem. 2003, 182.(h) For cyclization reactions with aminoketones: Thom, A.; Zinner, G. Arch. Pharm. (Weinheim, Ger.) 1994, 327, 469. (i) See also:Langer, P.; Bodtke, A. Tetrahedron Lett. 2003, 44, 5965. (j) For reactions with nitrile and malonate carbanions: Langer, P.; Albrecht, U. Synlett. 2003, 1503. (k) For an oxidative dimerization: Calestani, G.; Capella, L.; Leardini, R.; Minozzi, M.; Nanni, D.; Papa, R.; Romina, R.; Zanardi, G. Tetrahedron 2001, 57, 7221.
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29. 3OS (259.33): C, 60.21; H, 5.05; N, 16.20. Found: C, 60.61; H, 5.48; N, 16.46. All products were obtained as racemic material. All compounds gave correct spectroscopic data and satisfactory elemental analyses and/ or high resolution mass data.